Transition-Metal-Catalyzed Deuteration via Hydrogen Isotope Exchange

Abstract

Direct hydrogen isotope exchange represents a distinctive strategy for deuterium labelling, where the protium is directly replaced by deuterium. In this graphical review, we summarize the progress in deuteration via transition-metal-catalyzed hydrogen isotope exchange. The review is organized according to the mechanism of C–H bond activation relating to the homogeneous catalysis, and heterogeneous catalysis is also discussed according to the catalyst type. Representative mechanistic processes are depicted, and proven cases for tritiation are also highlighted.

Key words

H/D exchange - C–H activation - hydrogen-borrowing - deuterium labelling - heavy water - deuterium gas

Biosketches

Zhi-Jiang Jiang was born in 1990 in Ningbo, China. He obtained his B.Sc. in pharmaceutical science at Zhejiang University of Technology. He completed his Ph.D. under the supervision of Prof. Wei-Ke Su and Prof. Alexandre. V. Dushkin at the Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, where he explored the phenomenon of liquid-assisted grinding in mechanochemistry. He subsequently joined the School of Biological and Chemical Engineering of NingboTech University as an assistant professor in 2019. Currently, his research interests focus on the development of tools and strategies for selective deuterium-labelling.

Jian-Fei Bai graduated from Lanzhou University in 2007 and received his Ph.D. from the University of Chinese Academy of Sciences in 2012 under the supervision of Prof. Lixin Wang. In the same year, he joined the group of Prof. P. Vogel as a postdoctoral researcher at the Swiss Federal Institute of Technology in Lausanne (EPFL). He continued his postdoctoral studies at Kyoto University in 2015, working with Prof. Keiji Maruoka. In 2019, he was appointed as an associate professor at the Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, before moving to NingboTech University in 2021. His research focuses on the development and applications of the site-specific synthesis of deuterium-labeled compounds.

Zhanghua Gao obtained his Ph.D. in 2005 under the supervision of Prof. Wei-Dong Z. Li at Lanzhou University. In 2006, he joined the group of Prof. Philip J. Kocienski at the University of Leeds as a postdoctoral associate, undertaking research in natural product synthesis. After a one-year stay in the chemical industry, in 2010, he joined the University of Oxford as a postdoctoral fellow working with Prof. Véronique­ Gouverneur and Prof. Benjamin G. Davis on fluorine-18 radiolabeling of amino acids and proteins. In 2015, he moved to Ningbo University as an associate professor and became a full professor in 2016. His research interests include isotope-labelling methodology/technology and its applications in drug discovery and functional materials.

Deuterium labelling has become an increasingly important tool in biomedical and materials science, with its successful applications in drug development,[1] biological-compound imaging and tracking[2] and organic light-emitting diodes (OLEDs).[3] These applications have been accompanied by the development of synthetic strategies for efficient deuterium incorporation, such as conventional chemical transformations by catalytic hydrogenation of unsaturated bonds and the defunctionalization of aromatic halides.[4] Meanwhile, in contrast to the transformations of functional groups, the direct hydrogen isotope exchange (HIE) of C–H bonds has been extensively developed since the early days of deuterium incorporation, especially under a pH-dependent manner with harsh acid or base environments, which is still employed industrially in the mass production of deuterium compounds. Therefore, the development of milder and environmentally friendly deuteration strategies remains a necessity, especially methods that are compatible with economical deuterium sources, such as heavy water or deuterium gas.

Accompanied with an in-depth understanding of the characteristics of C–H activation with transition metals,[5] a few examples of transition-metal-facilitated HIE have been used as a chemical tool to check the reversibility of the process. Thus, benefiting from mechanistic investigations, catalytic HIE has been enabled based on reversible manipulation of established catalytic systems.[6] For instance, Crabtree’s catalyst, designed for hydrogenation, was found to facilitate dehydrogenation under a low H₂ pressure.[7a] This finding was further developed as a major type of HIE process based on reversible oxidative addition, catalyzed by a family of iridium catalysts such as Kerr’s catalysts,[8] [9] with D₂ gas as the main source of deuterium. Similar HIE processes have also been employed with Ir, Rh, Ru, and Pt,[10–12g,13,15] whilst earth-abundant metals such as Fe, Co and Ni also show promising reactivities.[12f–h,14] On the other hand, the recently burgeoning strategy of concerted metalation–deprotonation (CMD) was also utilized in a reversible manner,[16–22] which employed D₂O or deuterated acids as the deuterium source. Despite the challenge associated with CMD of subsequent route control between functionalization and C–D bond reconstruction, ortho- or meta-selective, as well as undirected deuteration, have been developed, mainly based on Pd catalysis;[20] [21] [22] however, Mn,[21a] Co,[18d] Ni,[18f] and Ag[19] have also been recently reported to show HIE activity. Moreover, HIE can also be accomplished through the strategy of hydrogen borrowing by exploiting the remarkable kinetic isotope effect of deuterium.[23] [24] As a reversible process, it has also been utilized in HIE with olefins.[25] Additionally, other specialized strategies have been reported, including Lewis acid enhanced local acidity of protons,[26] arene activation facilitated by an η⁶ complex,[27] and σ-metathesis-enabled H/D exchange between a metal and D₂.[28] On the other hand, heterogeneous catalysts also comprise a large family for HIE based on a similar strategy of reversibility control under low D₂ pressure,[31] [32] [33] [34] [35] [36] [37] where recent findings suggest that the nanoparticles collide,[38,39] and that the corresponding ligand-loaded nanoparticles[40] may also achieve astonishing regioselectivity compared to their homogeneous alternatives. Noticeably, in most cases, tritiation could be easily achieved by replacing the deuterium source with the corresponding tritium source. We hope that this graphical review will stimulate further research on the development of innovative HIE strategies within this rapidly evolving field.

Figure 1 HIE based on oxidative addition with directing groups (part 1): Early attempts using iridium catalysts[7`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n] [o] [p] and Kerr’s iridium catalysts[8a–k]

Figure 2 HIE based on oxidative addition with directing groups (part 2): Application of Kerr’s iridium catalysts[9`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m]

Figure 3 HIE based on oxidative addition with directing groups (part 3): Iridium catalysts with bidentate ligands[10`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 4 HIE based on oxidative addition without directing groups (part 1): Phosphine-ligand-supported metal catalysts[11`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n] [o] [p] [q] [r] [s] [t]

Figure 5 HIE based on oxidative addition without directing groups (part 2): Bipyridine-, imine-, and NHC-ligand-supported metal catalysts[12`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k]

Figure 6 HIE based on oxidative addition without directing groups (part 3): Tridentate-ligand-supported noble metal catalysts[13`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 7 HIE based on oxidative addition without directing groups (part 4): Tridentate-ligand-supported earth-abundant metal catalysts[14`] [b] [c] [d] [e]

Figure 8 HIE based on oxidative addition without directing groups (part 5): Half-sandwich-type metal catalysts[15`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m]

Figure 9 HIE based on concerted metalation–deprotonation (part 1): Directing-group-enabled ortho-selective deuteration[16`] [b] [c] [d] [e] [f] [g] [h]

Figure 10 HIE based on concerted metalation–deprotonation (part 2): Supporting-ligand- and bidentate-substrate-enabled regioselective deuteration[17`] [b] [c] [d] [e] [f] [g]

Figure 11 HIE based on concerted metalation–deprotonation (part 3): Regioselective deuteration of indoles, and earth-abundant-metal-catalyzed deuteration[18`] [b] [c] [d] [e] [f] [g] [h]

Figure 12 HIE based on concerted metalation–deprotonation (part 4): Silver-catalyzed deuteration[19`] [b] [c] [d] [e] [f] [g] and meta-selective deuteration[20a–f]

Figure 13 HIE based on concerted metalation–deprotonation (part 5): Application of a transient-directing-group (TDG) strategy[21`] [b] [c] [d] and a non-directing strategy in deuteration[22a–e]

Figure 14 HIE based on hydrogen borrowing (part 1): Principles, seminal work, and α-deuteration of alcohols via metal hydride intermediates[23`] [b] [c] [d] [e] [f]

Figure 15 HIE based on hydrogen borrowing (part 2): α- and β-deuteration of alcohols via ligand-enabled hydride transfer[23`] [h] [i] [j] [k] [l]

Figure 16 HIE based on hydrogen borrowing (part 3): Deuteration of amines, nitriles, and alkynes[24`] [b] [c] [d] [e] [f]

Figure 17 HIE based on iterative migratory insertion/β-elimination (part 1): Deuteration of olefins[25`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m]

Figure 18 HIE based on iterative migratory insertion/β-elimination (part 2): Deuteration of allyl groups and chain-walking deuteration.[25`] [o] [p] [q] [r] [s] Miscellaneous cases of homogeneous HIE (part 1): Lewis acid catalyzed deuteration[26a–c]

Figure 19 Miscellaneous cases of homogeneous HIE (part 2): Deuteration catalyzed by η⁶ complexes,[27a] [b] σ-metathesis,[28] π-acids[29] and metal chlorides[30`] [b] [c] [d]

Figure 20 Heterogeneous HIE catalyzed by an active-carbon-supported metal catalyst (part 1): Seminal work with PtO₂ [31`] [b] [c] [d] [e] and a Pd/C-H<sub>2</sub>-D<sub>2</sub>O system (part 1)[32`] [b] [c] [d] [e] [f]

Figure 21 Heterogeneous HIE catalyzed by an active-carbon-supported metal catalyst (part 2): A Pd/C-H₂-D₂O system (part 2)[32`] [h] [i] [j] [k] [l] [m] [n] [o]

Figure 22 Heterogeneous HIE catalyzed by an active-carbon-supported metal catalyst (part 3): Further applications of M/C-H₂-D₂O systems, Pt/C,[33`] [b] [c] [d] Rh/C[34a–e] and Ru/C[35a–c]

Figure 23 Heterogeneous HIE catalyzed by an active-carbon-supported metal catalyst (part 4): M/C- ⁱ PrOH-D₂O[36`] [b] [c] [d] [e] [f] [g] and Pt/C- ⁿ BuNH₂-D₂O[37] systems

Figure 24 Heterogeneous HIE catalyzed by metal nanoparticles (part 1): PVP-supported metal nanoparticles[38`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Figure 25 Heterogeneous HIE catalyzed by metal nanoparticles (part 2): NHC-supported metal nanoparticles (part 1)[39`] [b] [c] [d] [e] [f] [g]

Figure 26 Heterogeneous HIE catalyzed by metal nanoparticles (part 3): NHC-supported metal nanoparticles (part 2)[39h] [i] and pyrolytic-carbon-supported novel metal nanoparticles[40a–f]

Conflict of Interest

The authors declare no conflict of interest.

Acknowledgment

We are grateful to Professor Bencan Tang of the University of Nottingham Ningbo China for constructive discussions, and to current and former members of the Gao group who have contributed to the development of this field. We also thank Ningbo Cuiying Chemical Technology Co. Ltd. for their continuous support of our research in this field.

• References

• 1a Cargnin S, Serafini M, Pirali T. Future Med. Chem. 2019; 11: 2039
• 1b Pirali T, Serafini M, Cargnin S, Genazzani AA. J. Med. Chem. 2019; 62: 5276
• 1c Di Martino RM. C, Maxwell BD, Pirali T. Nat. Rev. Drug Discovery 2023; 22: 562
• 1d Wang X, Luo Y.-B, Luo Y.-X, Liu M.-C, Lu C.-H, Song R.-J. Appl. Organomet. Chem. 2024; 38: e7602
• 1e Derdau V, Elmore CS, Hartung T, McKillican B, Mejuch T, Rosenbaum C, Wiebe C. Angew. Chem. Int. Ed. 2023; 62: e202306019
• 2a Asano H, Elhelaly AE, Hyodo F, Iwasaki R, Noda Y, Kato H, Ichihashi K, Tomita H, Murata M, Mori T, Matsuo M. Clin. Cancer Res. 2023; 29: 5173
• 2b Chahrour O, Cobice D, Malone J. J. Pharm. Biomed. Anal. 2015; 113: 2
• 2c Chokkathukalam A, Kim DH, Barrett MP, Breitling R, Creek DJ. Bioanalysis 2014; 6: 511
• 3a Montenegro E, Ganss S, Bürger M, Correia C, Lackner A, Stolz S, Kröber J, Hayer A, Engelhart J, Linge R, Na W.-K, Na S.-H. SID Symp. Dig. Tech. Pap. 2024; 55: 721
• 3b Cheng J.-F, Kong F.-C, Zhang K, Cai J.-H, Zhao Y, Wang C.-K, Fan J, Liao L.-S. Chem. Eng. J. 2022; 430: 132822
• 3c Peng X, Yeh CH, Wang SF, Yan J, Gan S, Su SJ, Zhou X, Zhang YX, Chi Y. Adv. Opt. Mater. 2022; 10: 2201291
• 3d Bae HJ, Kim JS, Yakubovich A, Jeong J, Park S, Chwae J, Ishibe S, Jung Y, Rai VK, Son WJ, Kim S, Choi H, Baik MH. Adv. Opt. Mater. 2021; 9: 2100630
• 4a Norcott PL. Chem. Commun. 2022; 58: 2944
• 4b Kopf S, Bourriquen F, Li W, Neumann H, Junge K, Beller M. Chem. Rev. 2022; 122: 6634
• 4c Li N, Li Y, Wu X, Zhu C, Xie J. Chem. Soc. Rev. 2022; 51: 6291
• 4d Zhou R, Ma L, Yang X, Cao J. Org. Chem. Front. 2021; 8: 426
• 4e Lepron M, Daniel-Bertrand M, Mencia G, Chaudret B, Feuillastre S, Pieters G. Acc. Chem. Res. 2021; 54: 1465
• 4f Vang ZP, Hintzsche SJ, Clark JR. Chem. Eur. J. 2021; 27: 9988
• 5a Altus KM, Love JA. Commun. Chem. 2021; 4: 173
• 5b Dalton T, Faber T, Glorius F. ACS. Cent. Sci. 2021; 7: 245
• 5c Docherty JH, Lister TM, McArthur G, Findlay MT, Domingo-Legarda P, Kenyon J, Choudhary S, Larrosa I. Chem. Rev. 2023; 123: 7692
• 5d Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primers 2021; 1: 43
• 6a Prakash G, Paul N, Oliver GA, Werz DB, Maiti D. Chem. Soc. Rev. 2022; 51: 3123
• 6b Kang Q.-K, Shi H. Synlett 2021; 33: 329
• 6c Atzrodt J, Derdau V, Kerr WJ, Reid M. Angew. Chem. Int. Ed. 2018; 57: 3022
• 6d Atzrodt J, Derdau V, Fey T, Zimmermann J. Angew. Chem. Int. Ed. 2007; 46: 7744
• 7a Hesk D, Das PR, Evans B. J. Labelled Compd. Radiopharm. 1995; 36: 497
• 7b Kingston LP, Lockley WJ. S, Mather AN, Spink E, Thompson SP, Wilkinson DJ. Tetrahedron Lett. 2000; 41: 2705
• 7c Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, McAuley BM, Wilkinson DJ. Tetrahedron Lett. 2003; 44: 3959
• 7d McAuley B, Hickey MJ, Kingston LP, Jones JR, Lockley WJ. S, Mather AN, Spink E, Thompson SP, Wilkinson DJ. J. Labelled Compd. Radiopharm. 2003; 46: 1191
• 7e Garman RN, Hickey MJ, Kingston LP, McAuley B, Jones JR, Lockley WJ. S, Mather AN, Wilkinson DJ. J. Labelled Compd. Radiopharm. 2005; 48: 75
• 7f Heys R. J. Chem. Soc., Chem. Commun. 1992; 680
• 7g Heys JR, Shu AY. L, Senderoff SG, Phillips NM. J. Labelled Compd. Radiopharm. 1993; 33: 431
• 7h Shu AY. L, Chen W, Heys JR. J. Organomet. Chem. 1996; 524: 87
• 7i Chen W, Garnes KT, Levinson SH, Saunders D, Senderoff SG, Shu AY. L, Villani AJ, Heys JR. J. Labelled Compd. Radiopharm. 1997; 39: 291
• 7j Shu AY. L, Saunders D, Levinson SH, Landvatter SW, Mahoney A, Senderoff SG, Mack JF, Heys JR. J. Labelled Compd. Radiopharm. 1999; 42: 797
• 7k Shu AY. L, Heys JR. Tetrahedron Lett. 2000; 41: 9015
• 7l Ellames GJ, Gibson JS, Herbert JM, McNeill AH. Tetrahedron 2001; 57: 9487
• 7m Cross PW. C, Ellames GJ, Gibson JS, Herbert JM, Kerr WJ, McNeill AH, Mathers TW. Tetrahedron 2003; 59: 3349
• 7n Ellames GJ, Gibson JS, Herbert JM, Kerr WJ, McNeill AH. J. Labelled Compd. Radiopharm. 2004; 47: 1
• 7o Salter R, Bosser I. J. Labelled Compd. Radiopharm. 2003; 46: 489
• 7p Krüger J, Manmontri B, Fels G. Eur. J. Org. Chem. 2005; 1402
• 8a Brown JA, Irvine S, Kennedy AR, Kerr WJ, Andersson S, Nilsson GN. Chem. Commun. 2008; 1115
• 8b Nilsson GN, Kerr WJ. J. Labelled Compd. Radiopharm. 2010; 53: 662
• 8c Cochrane AR, Irvine S, Kerr WJ, Reid M, Andersson S, Nilsson GN. J. Labelled Compd. Radiopharm. 2013; 56: 451
• 8d Cross P, Herbert J, Kerr W, McNeill A, Paterson L. Synlett 2015; 27: 111
• 8e Kerr WJ, Knox GJ, Reid M, Tuttle T. Chem. Sci. 2021; 12: 6747
• 8f Cochrane AR, Idziak C, Kerr WJ, Mondal B, Paterson LC, Tuttle T, Andersson S, Nilsson GN. Org. Biomol. Chem. 2014; 12: 3598
• 8g Kennedy AR, Kerr WJ, Moir R, Reid M. Org. Biomol. Chem. 2014; 12: 7927
• 8h Kerr WJ, Mudd RJ, Owens PK, Reid M, Brown JA, Campos S. J. Labelled Compd. Radiopharm. 2016; 59: 601
• 8i Brown JA, Cochrane AR, Irvine S, Kerr WJ, Mondal B, Parkinson JA, Paterson LC, Reid M, Tuttle T, Andersson S, Nilsson GN. Adv. Synth. Catal. 2014; 356: 3551
• 8j Timofeeva DS, Lindsay DM, Kerr WJ, Nelson DJ. Catal. Sci. Technol. 2020; 10: 7249
• 8k Timofeeva DS, Lindsay DM, Kerr WJ, Nelson DJ. Catal. Sci. Technol. 2021; 11: 5498
• 8l Morawietz P, Weck R, Scholte AA, Atzrodt J, Güssregen S, Derdau V. Green Chem. 2022; 24: 4824
• 9a Devlin J, Kerr W, Lindsay D, McCabe T, Reid M, Tuttle T. Molecules 2015; 20: 11676
• 9b Kerr WJ, Mudd RJ, Paterson LC, Brown JA. Chem. Eur. J. 2014; 20: 14604
• 9c Valero M, Weck R, Güssregen S, Atzrodt J, Derdau V. Angew. Chem. Int. Ed. 2018; 57: 8159
• 9d Atzrodt J, Derdau V, Kerr WJ, Reid M, Rojahn P, Weck R. Tetrahedron 2015; 71: 1924
• 9e Kerr WJ, Lindsay DM, Reid M, Atzrodt J, Derdau V, Rojahn P, Weck R. Chem. Commun. 2016; 52: 6669
• 9f Kerr WJ, Reid M, Tuttle T. ACS Catal. 2015; 5: 402
• 9g Kerr WJ, Mudd RJ, Reid M, Atzrodt J, Derdau V. ACS Catal. 2018; 8: 10895
• 9h Knight NM. L, Thompson JD. F, Parkinson JA, Lindsay DM, Tuttle T, Kerr WJ. Adv. Synth. Catal. 2024; 366: 2577
• 9i Kerr WJ, Reid M, Tuttle T. Angew. Chem. Int. Ed. 2017; 56: 7808
• 9j Kerr WJ, Lindsay DM, Owens PK, Reid M, Tuttle T, Campos S. ACS Catal. 2017; 7: 7182
• 9k Koneczny M, Phong Ho L, Nasr A, Freytag M, Jones PG, Tamm M. Adv. Synth. Catal. 2020; 362: 3857
• 9l Liu W, Cao L, Zhang Z, Zhang G, Huang S, Huang L, Zhao P, Yan X. Org. Lett. 2020; 22: 2210
• 9m Zhao L.-L, Wu Y, Huang S, Zhang Z, Liu W, Yan X. Org. Lett. 2021; 23: 9297
• 10a Parmentier M, Hartung T, Pfaltz A, Muri D. Chem. Eur. J. 2014; 20: 11496
• 10b Jess K, Derdau V, Weck R, Atzrodt J, Freytag M, Jones PG, Tamm M. Adv. Synth. Catal. 2017; 359: 629
• 10c Valero M, Burhop A, Jess K, Weck R, Tamm M, Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2018; 61: 380
• 10d Valero M, Becker D, Jess K, Weck R, Atzrodt J, Bannenberg T, Derdau V, Tamm M. Chem. Eur. J. 2019; 25: 6517
• 10e Becker D, Bockfeld D, Tamm M. Adv. Synth. Catal. 2022; 365: 367
• 10f Burhop A, Weck R, Atzrodt J, Derdau V. Eur. J. Org. Chem. 2017; 1418
• 10g Burhop A, Prohaska R, Weck R, Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2017; 60: 343
• 10h Valero M, Mishra A, Blass J, Weck R, Derdau V. ChemistryOpen 2019; 8: 1183
• 10i Kerr WJ, Knox GJ, Reid M, Tuttle T, Bergare J, Bragg RA. ACS Catal. 2020; 10: 11120
• 11a Garnett JL, Hodges RJ. Chem. Commun. 1967; 1220
• 11b Garnett JL, Hodges RJ. J. Am. Chem. Soc. 1967; 89: 4546
• 11c Hodges RJ, Garnett JL. J. Phys. Chem. 1968; 72: 1673
• 11d Hodges RJ, Garnett JL. J. Phys. Chem. 1969; 73: 1525
• 11e Garnett JL, Kenyon RS. J. Chem. Soc. D 1970; 698
• 11f Garnett JL, Kenyon RS. J. Chem. Soc. D 1971; 1227
• 11g Garnett JL, Long MA, McLaren AB, Peterson KB. J. Chem. Soc., Chem. Commun. 1973; 749
• 11h Blake MR, Garnett JL, Gregor IK, Hannan W, Hoa K, Long MA. J. Chem. Soc., Chem. Commun. 1975; 930
• 11i Gröll B, Schnürch M, Mihovilovic MD. J. Org. Chem. 2012; 77: 4432
• 11j Chen S, Song G, Li X. Tetrahedron Lett. 2008; 49: 6929
• 11k Eisele P, Ullwer F, Scholz S, Plietker B. Chem. Eur. J. 2019; 25: 16550
• 11l Eguillor B, Esteruelas MA, García-Raboso J, Oliván M, Oñate E. Organometallics 2009; 28: 3700
• 11m Alexakis E, Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, Smith T, Wilkinson DJ. Tetrahedron Lett. 2005; 46: 4291
• 11n Chaudret B. J. Organomet. Chem. 1984; 268: c33
• 11o Kratish Y, Bravo-Zhivotovskii D, Apeloig Y. ACS Omega 2017; 2: 372
• 11p Colebatch AL, Weller AS. Chem. Eur. J. 2018; 24: 5450
• 11q Connor BA, Rittle J, VanderVelde D, Peters JC. Organometallics 2016; 35: 686
• 11r Fryzuk MD, Rosenberg L, Rettig SJ. Organometallics 1991; 10: 2537
• 11s Ayed T, Barthelat J.-C, Tangour B, Pradère C, Donnadieu B, Grellier M, Sabo-Etienne S. Organometallics 2005; 24: 3824
• 11t Smart KA, Mothes Martin E, Annaka T, Grellier M, Sabo Etienne S. Adv. Synth. Catal. 2014; 356: 759
• 12a Hickman AJ, Villalobos JM, Sanford MS. Organometallics 2009; 28: 5316
• 12b Villalobos JM, Hickman AJ, Sanford MS. Organometallics 2010; 29: 257
• 12c Emmert MH, Gary JB, Villalobos JM, Sanford MS. Angew. Chem. Int. Ed. 2010; 49: 5884
• 12d Gary JB, Carter TJ, Sanford MS. Top. Catal. 2012; 55: 565
• 12e Hickman AJ, Cismesia MA, Sanford MS. Organometallics 2012; 31: 1761
• 12f Palmer WN, Chirik PJ. ACS Catal. 2017; 7: 5674
• 12g Yang H, Zarate C, Palmer WN, Rivera N, Hesk D, Chirik PJ. ACS Catal. 2018; 8: 10210
• 12h Zarate C, Yang H, Bezdek MJ, Hesk D, Chirik PJ. J. Am. Chem. Soc. 2019; 141: 5034
• 12i Giunta D, Hölscher M, Lehmann CW, Mynott R, Wirtz C, Leitner W. Adv. Synth. Catal. 2003; 345: 1139
• 12j Chen Q, Liu Q, Xiao J, Leng X, Deng L. J. Am. Chem. Soc. 2021; 143: 19956
• 12k Nelson DJ, Egbert JD, Nolan SP. Dalton Trans. 2013; 42: 4105
• 12l Fortman GC, Jacobsen H, Cavallo L, Nolan SP. Chem. Commun. 2011; 47: 9723
• 13a Iluc VM, Fedorov A, Grubbs RH. Organometallics 2012; 31: 39
• 13b Polukeev AV, Marcos R, Ahlquist MS. G, Wendt OF. Organometallics 2016; 35: 2600
• 13c Prechtl MH. G, Hölscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W. Angew. Chem. Int. Ed. 2007; 46: 2269
• 13d Prechtl MH. G, Hölscher M, Ben-David Y, Theyssen N, Milstein D, Leitner W. Eur. J. Inorg. Chem. 2008; 3493
• 13e Ng SM, Lam WH, Mak CC, Tsang CW, Jia G, Lin Z, Lau CP. Organometallics 2003; 22: 641
• 13f Leung CW, Zheng W, Wang D, Ng SM, Yeung CH, Zhou Z, Lin Z, Lau CP. Organometallics 2007; 26: 1924
• 13g Rhinehart JL, Manbeck KA, Buzak SK, Lippa GM, Brennessel WW, Goldberg KI, Jones WD. Organometallics 2012; 31: 1943
• 13h Esteruelas MA, Martínez A, Oliván M, Vélez A. J. Org. Chem. 2020; 85: 15693
• 13i Kramer M, Watts D, Vedernikov AN. Organometallics 2020; 39: 4102
• 14a Pony Yu R, Hesk D, Rivera N, Pelczer I, Chirik PJ. Nature 2016; 529: 195
• 14b Corpas J, Viereck P, Chirik PJ. ACS Catal. 2020; 10: 8640
• 14c Garhwal S, Kaushansky A, Fridman N, Shimon LJ. W, de Ruiter G. J. Am. Chem. Soc. 2020; 142: 17131
• 14d Cummins AW. M, Li S, Willcox DR, Muilu T, Docherty JH, Thomas SP. Tetrahedron 2020; 76: 131084
• 14e Roque JB, Pabst TP, Chirik PJ. ACS Catal. 2022; 12: 8877
• 15a Golden JT, Andersen RA, Bergman RG. J. Am. Chem. Soc. 2001; 123: 5837
• 15b Yung CM, Skaddan MB, Bergman RG. J. Am. Chem. Soc. 2004; 126: 13033
• 15c Klei SR, Golden JT, Tilley TD, Bergman RG. J. Am. Chem. Soc. 2002; 124: 2092
• 15d Skaddan MB, Yung CM, Bergman RG. Org. Lett. 2004; 6: 11
• 15e Skaddan MB, Bergman RG. J. Labelled Compd. Radiopharm. 2006; 49: 623
• 15f Corberán R, Sanaú M, Peris E. J. Am. Chem. Soc. 2006; 128: 3974
• 15g Feng Y, Jiang B, Boyle PA, Ison EA. Organometallics 2010; 29: 2857
• 15h Lehman MC, Gary JB, Boyle PD, Sanford MS, Ison EA. ACS Catal. 2013; 3: 2304
• 15i Mai VH, Gadzhiev OB, Ignatov SK, Nikonov GI. Catal. Sci. Technol. 2019; 9: 3398
• 15j Piola L, Fernández-Salas JA, Manzini S, Nolan SP. Org. Biomol. Chem. 2014; 12: 8683
• 15k Prades A, Poyatos M, Peris E. Adv. Synth. Catal. 2010; 352: 1155
• 15l Zhao L.-L, Liu W, Zhang Z, Zhao H, Wang Q, Yan X. Org. Lett. 2019; 21: 10023
• 15m Campos J, Esqueda AC, López-Serrano J, Sánchez L, Cossio FP, De Cozar A, Álvarez E, Maya C, Carmona E. J. Am. Chem. Soc. 2010; 132: 16765
• 16a Gorelsky SI, Lapointe D, Fagnou K. J. Am. Chem. Soc. 2008; 130: 10848
• 16b Ackermann L. Chem. Rev. 2011; 111: 1315
• 16c Wu K, Lam N, Strassfeld DA, Fan Z, Qiao JX, Liu T, Stamos D, Yu JQ. Angew. Chem. Int. Ed. 2024; 63: e202400509
• 16d Ma S, Villa G, Thuy-Boun PS, Homs A, Yu J.-Q. Angew. Chem. Int. Ed. 2014; 53: 734
• 16e Müller V, Weck R, Derdau V, Ackermann L. ChemCatChem 2020; 12: 100
• 16f Garreau AL, Zhou H, Young MC. Org. Lett. 2019; 21: 7044
• 16g Zhang Z, Jiang Z.-J, Cao Y, Chen J, Gao Z. Synthesis 2022; 54: 4907
• 16h Hirano M, Fujimoto R, Hatagami K, Komine N, Komiya S. ChemCatChem 2013; 5: 1101
• 17a Giles R, Ahn G, Jung KW. Tetrahedron Lett. 2015; 56: 6231
• 17b Uttry A, Mal S, van Gemmeren M. J. Am. Chem. Soc. 2021; 143: 10895
• 17c Zheng C, Xue J, Jiang ZJ, Han J, Wang J, Bai JF, Chen J, Gao Z. Chem. Commun. 2024; 60: 10338
• 17d Liu W, Xu X, Zhao H, Yan X. Tetrahedron 2018; 74: 4111
• 17e Zhao D, Luo H, Chen B, Chen W, Zhang G, Yu Y. J. Org. Chem. 2018; 83: 7860
• 17f Sheng F.-F, Gu J.-G, Liu K.-H, Zhang H.-H. J. Org. Chem. 2022; 87: 16084
• 17g Yin D.-W, Liu G. J. Org. Chem. 2018; 83: 3987
• 18a Fitzgerald LS, McNulty RL, Greener A, O’Duill ML. J. Org. Chem. 2023; 88: 10772
• 18b Wu J, Qian B, Lu L, Yang H, Shang Y, Zhang J. Org. Chem. Front. 2021; 8: 3032
• 18c Peng W, Liu Q, Yin F, Shi C, Ji L, Qu L, Wang C, Luo H, Kong L, Wang X. RSC Adv. 2021; 11: 8356
• 18d Zhang J, Zhang S, Gogula T, Zou H. ACS Catal. 2020; 10: 7486
• 18e Ko SL, Courtney E, Light DM, Jones DD, McGlacken DG. P. Tetrahedron Green Chem 2023; 2: 100019
• 18f Jiang Z.-J, Xu S.-H, Su Y, Hu E, Han J, Bai J.-F, Tang B, Chen J, Gao Z. Chem. Commun. 2024; 60: 384
• 18g Young KJ. H, Lokare KS, Leung CH, Cheng M.-J, Nielsen RJ, Petasis NA, Goddard WA, Periana RA. J. Mol. Catal. A: Chem. 2011; 339: 17
• 18h Su Y, Jiang Z.-J, Han J, Duan L, Bai J.-F, Chen J, Gao Z. Chem. Eur. J. 2024; in press; DOI
• 19a Li E.-C, Hu G.-Q, Zhu Y.-X, Zhang H.-H, Shen K, Hang X.-C, Zhang C, Huang W. Org. Lett. 2019; 21: 6745
• 19b Tlahuext-Aca A, Hartwig JF. ACS Catal. 2021; 11: 1119
• 19c Sheng F.-F, Li E.-C, Bai J.-W, Wang C.-X, Hu G.-Q, Liu K.-H, Sun Z.-Y, Shen K, Zhang H.-H. Org. Biomol. Chem. 2022; 20: 1176
• 19d Hu G.-Q, Li E.-C, Zhang H.-H, Huang W. Org. Biomol. Chem. 2020; 18: 6627
• 19e Hu G.-Q, Bai J.-W, Li E.-C, Liu K.-H, Sheng F.-F, Zhang H.-H. Org. Lett. 2021; 23: 1554
• 19f Tang J, Kong J, Xu H, Jiang Z.-J, She Y, Bai J, Tang B, Chen J, Gao Z, Gao K. J. Org. Chem. 2023; 88: 1560
• 19g Xu H, Jiang ZJ, Jia Y, Su Y, Bai JF, Gao Z, Chen J, Gao K. J. Org. Chem. 2024; 89: 8468
• 20a Leow D, Li G, Mei TS, Yu JQ. Nature 2012; 486: 518
• 20b Tang RY, Li G, Yu JQ. Nature 2014; 507: 215
• 20c Dey A, Sinha SK, Achar TK, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10820
• 20d Dutta U, Maiti D. Acc. Chem. Res. 2022; 55: 354
• 20e Bag S, Petzold M, Sur A, Bhowmick S, Werz DB, Maiti D. Chem. Eur. J. 2019; 25: 9433
• 20f Xu H, Liu M, Li L.-J, Cao Y.-F, Yu J.-Q, Dai H.-X. Org. Lett. 2019; 21: 4887
• 21a Kopf S, Neumann H, Beller M. Chem. Commun. 2021; 57: 1137
• 21b Kong J, Jiang Z.-J, Xu J, Li Y, Cao H, Ding Y, Tang B, Chen J, Gao Z. J. Org. Chem. 2021; 86: 13350
• 21c Zheng C, Jiang Z.-J, Jin K, Wang Q, Bai J.-F, Xu G, Gao Z. J. Org. Chem. 2023; 88: 17164
• 21d Kopf S, Ye F, Neumann H, Beller M. Chem. Eur. J. 2021; 27: 9768
• 22a Farizyan M, Mondal A, Mal S, Deufel F, van Gemmeren M. J. Am. Chem. Soc. 2021; 143: 16370
• 22b Dey J, Kaltenberger S, van Gemmeren M. Angew. Chem. Int. Ed. 2024; 63: e202404421
• 22c Dey J, van Gemmeren M. Synlett 2024; 35: 2191
• 22d Yun SJ, Kim J, Kang E, Jung H, Kim HT, Kim M, Joo JM. ACS Catal. 2023; 13: 4042
• 22e Werz DB, Teja C, Kolb S, Colonna P, Grover J, Lahiri GK, Pieters G, Maiti D, Garcia-Argote S. Angew. Chem. Int. Ed. 2024; 63: e202410162
• 23a Reed-Berendt BG, Latham DE, Dambatta MB, Morrill LC. ACS. Cent. Sci. 2021; 7: 570
• 23b Corma A, Navas J, Sabater MJ. Chem. Rev. 2018; 118: 1410
• 23c Michelotti A, Roche M. Synthesis 2019; 51: 1319
• 23d Takahashi M, Oshima K, Matsubara S. Chem. Lett. 2005; 34: 192
• 23e Bossi G, Putignano E, Rigo P, Baratta W. Dalton Trans. 2011; 40: 8986
• 23f Itoga M, Yamanishi M, Udagawa T, Kobayashi A, Maekawa K, Takemoto Y, Naka H. Chem. Sci. 2022; 13: 8744
• 23g Chatterjee B, Gunanathan C. Org. Lett. 2015; 17: 4794
• 23h Zhang L, Nguyen DH, Raffa G, Desset S, Paul S, Dumeignil F, Gauvin RM. Catal. Commun. 2016; 84: 67
• 23i Kar S, Goeppert A, Sen R, Kothandaraman J, Prakash GK. S. Green Chem. 2018; 20: 2706
• 23j Khaskin E, Milstein D. ACS Catal. 2013; 3: 448
• 23k Tse SK. S, Xue P, Lau CW. S, Sung HH. Y, Williams ID, Jia G. Chem. Eur. J. 2011; 17: 13918
• 23l Bai W, Lee K.-H, Tse SK. S, Chan KW, Lin Z, Jia G. Organometallics 2015; 34: 3686
• 24a Neubert L, Michalik D, Bähn S, Imm S, Neumann H, Atzrodt J, Derdau V, Holla W, Beller M. J. Am. Chem. Soc. 2012; 134: 12239
• 24b Chatterjee B, Krishnakumar V, Gunanathan C. Org. Lett. 2016; 18: 5892
• 24c Hale LV. A, Szymczak NK. J. Am. Chem. Soc. 2016; 138: 13489
• 24d Krishnakumar V, Gunanathan C. Chem. Commun. 2018; 54: 8705
• 24e Guo B, Vries JG, Otten E. Adv. Synth. Catal. 2022; 364: 179
• 24f Chatterjee B, Gunanathan C. Chem. Commun. 2016; 52: 4509
• 25a Faller JW, Smart CJ. Organometallics 1989; 8: 602
• 25b Kohl G, Rudolph R, Pritzkow H, Enders M. Organometallics 2005; 24: 4774
• 25c Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Lahoz FJ, Oro LA. Chem. Eur. J. 2014; 20: 8391
• 25d Lenges CP, White PS, Brookhart M. J. Am. Chem. Soc. 1999; 121: 4385
• 25e Lenges CP, White PS, Marshall WJ, Brookhart M. Organometallics 2000; 19: 1247
• 25f Lenges CP, Brookhart M. J. Am. Chem. Soc. 1997; 119: 3165
• 25g Lenges CP, Brookhart M, Grant BE. J. Organomet. Chem. 1997; 528: 199
• 25h Lenges CP, White PS, Brookhart M. J. Am. Chem. Soc. 1998; 120: 6965
• 25i Tse SK. S, Xue P, Lin Z, Jia G. Adv. Synth. Catal. 2010; 352: 1512
• 25j Camedda N, Serafino A, Maggi R, Bigi F, Cera G, Maestri G. Synthesis 2020; 52: 1762
• 25k Hatano M, Nishimura T, Yorimitsu H. Org. Lett. 2016; 18: 3674
• 25l Bechtoldt A, Ackermann L. ChemCatChem 2019; 11: 435
• 25m Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Lahoz FJ, Polo V, Oro LA. Angew. Chem. Int. Ed. 2011; 50: 3938
• 25n Erdogan G, Grotjahn DB. J. Am. Chem. Soc. 2009; 131: 10354
• 25o Erdogan G, Grotjahn DB. Top. Catal. 2010; 53: 1055
• 25p Smarun AV, Petković M, Shchepinov MS, Vidović D. J. Org. Chem. 2017; 82: 13115
• 25q Cramer R. J. Am. Chem. Soc. 1966; 88: 2272
• 25r Ishibashi K, Takahashi M, Yokota Y, Oshima K, Matsubara S. Chem. Lett. 2005; 34: 664
• 25s Cera G, Della Ca’ N, Maestri G. Chem. Sci. 2019; 10: 10297
• 26a Dong B, Cong X, Hao N. RSC Adv. 2020; 10: 25475
• 26b Bourriquen F, Junge K, Beller M. Synlett 2023; 34: 332
• 26c Bai J.-W, Guo L, Chen M.-Z, Advincula R, Zhang H.-H. Tetrahedron Lett. 2024; 135: 154884
• 27a Kang QK, Li Y, Chen K, Zhu H, Wu WQ, Lin Y, Shi H. Angew. Chem. Int. Ed. 2022; 61: e202117381
• 27b Lu J.-L, Deng J.-T, Lang M, Peng J.-B. Org. Chem. Front. 2024; 11: 5473
• 28 Linford-Wood TG, Mahon MF, Grayson MN, Webster RL. ACS Catal. 2022; 12: 2979
• 29 Wu D.-C, Bai J.-W, Guo L, Hu G.-Q, Liu K.-H, Sheng F.-F, Zhang H.-H, Sun Z.-Y, Shen K, Liu X. Tetrahedron Lett. 2021; 66: 152807
• 30a Guo Q.-X, Shen B.-J, Guo H.-Q, Takahashi T. Chin. J. Chem. 2005; 23: 341
• 30b Garnett JL, Long MA, Vining RF. W, Mole T. J. Am. Chem. Soc. 1972; 94: 5913
• 30c Long MA, Garnett JL, Vining RF. W, Mole T. J. Am. Chem. Soc. 1972; 94: 8632
• 30d Long MA, Garnett JL, Vining RF. W. J. Chem. Soc., Perkin Trans. 2 1975; 1298
• 31a Brown WG, Garnett JL. J. Am. Chem. Soc. 1958; 80: 5272
• 31b Norton R. J. Catal. 1975; 39: 53
• 31c Maeda M, Ogawa O, Kawazoe Y. Chem. Pharm. Bull. 1977; 25: 3329
• 31d Yamamoto M, Yokota Y, Oshima K, Matsubara S. Chem. Commun. 2004; 1714
• 31e Barthez JM, Filikov AV, Frederiksen LB, Huguet M.-L, Jones JR, Lu S.-Y. Can. J. Chem. 1998; 76: 726
• 32a Sajiki H, Hattori K, Aoki F, Yasunaga K, Hirota K. Synlett 2002; 1149
• 32b Sajiki H, Aoki F, Esaki H, Maegawa T, Hirota K. Org. Lett. 2004; 6: 1485
• 32c Esaki H, Aoki F, Umemura M, Kato M, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2007; 13: 4052
• 32d Kurita T, Hattori K, Seki S, Mizumoto T, Aoki F, Yamada Y, Ikawa K, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2008; 14: 664
• 32e Sajiki H, Kurita T, Esaki H, Aoki F, Maegawa T, Hirota K. Org. Lett. 2004; 6: 3521
• 32f Kurita T, Aoki F, Mizumoto T, Maejima T, Esaki H, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2008; 14: 3371
• 32g Sajiki H, Ito N, Esaki H, Maesawa T, Maegawa T, Hirota K. Tetrahedron Lett. 2005; 46: 6995
• 32h Derdau V, Atzrodt J, Zimmermann J, Kroll C, Brückner F. Chem. Eur. J. 2009; 15: 10397
• 32i Shen H, Liu Y, Tian X, Zhang X, Zhang Y. ChemistrySelect 2018; 3: 8724
• 32j Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Synlett 2005; 1385
• 32k Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Heterocycles 2005; 66: 361
• 32l Esaki H, Ohtaki R, Maegawa T, Monguchi Y, Sajiki H. J. Org. Chem. 2007; 72: 2143
• 32m Maegawa T, Akashi A, Esaki H, Aoki F, Sajiki H, Hirota K. Synlett 2005; 845
• 32n Esaki H, Ito N, Sakai S, Maegawa T, Monguchi Y, Sajiki H. Tetrahedron 2006; 62: 10954
• 32o Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2010; 53: 674
• 33a Ito N, Esaki H, Maesawa T, Imamiya E, Maegawa T, Sajiki H. Bull. Chem. Soc. Jpn. 2008; 81: 278
• 33b Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Adv. Synth. Catal. 2006; 348: 1025
• 33c Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Synthesis 2008; 1467
• 33d Maegawa T, Ito N, Oono K, Monguchi Y, Sajiki H. Synthesis 2009; 2674
• 34a Maegawa T, Fujiwara Y, Inagaki Y, Esaki H, Monguchi Y, Sajiki H. Angew. Chem. Int. Ed. 2008; 47: 5394
• 34b Fujiwara Y, Iwata H, Sawama Y, Monguchi Y, Sajiki H. Chem. Commun. 2010; 46: 4977
• 34c Cioffi EA. Tetrahedron Lett. 1996; 37: 6231
• 34d Cioffi EA, Willis WS, Suib SL. Langmuir 1990; 6: 404
• 34e Cioffi EA, Willis WS, Suib SL. Langmuir 1988; 4: 697
• 35a Gao L, Perato S, Garcia-Argote S, Taglang C, Martínez-Prieto LM, Chollet C, Buisson D.-A, Dauvois V, Lesot P, Chaudret B, Rousseau B, Feuillastre S, Pieters G. Chem. Commun. 2018; 54: 2986
• 35b Maegawa T, Fujiwara Y, Inagaki Y, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2008; 350: 2215
• 35c Sawama Y, Yabe Y, Iwata H, Fujiwara Y, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16436
• 36a Sawama Y, Yamada T, Yabe Y, Morita K, Shibata K, Shigetsura M, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2013; 355: 1529
• 36b Yamada T, Sawama Y, Shibata K, Morita K, Monguchi Y, Sajiki H. RSC Adv. 2015; 5: 13727
• 36c Yamada T, Park K, Yasukawa N, Morita K, Monguchi Y, Sawama Y, Sajiki H. Adv. Synth. Catal. 2016; 358: 3277
• 36d Park K, Matsuda T, Yamada T, Monguchi Y, Sawama Y, Doi N, Sasai Y, Kondo S. i, Sawama Y, Sajiki H. Adv. Synth. Catal. 2018; 360: 2303
• 36e Sawama Y, Nakano A, Matsuda T, Kawajiri T, Yamada T, Sajiki H. Org. Process Res. Dev. 2019; 23: 648
• 36f Sawama Y, Matsuda T, Moriyama S, Ban K, Fujioka H, Kamiya M, Shou J, Ozeki Y, Akai S, Sajiki H. Asian J. Org. Chem. 2023; 12: e202200710
• 36g Moriyama S, Mae M, Shibata D, Yamakoshi H, Kajimoto S, Nakabayashi T, Ishimoto T, Mogi K, Sajiki H, Akai S, Sawama Y. Chem. Commun. 2023; 59: 12100
• 37 Park K, Oka N, Sawama Y, Ikawa T, Yamada T, Sajiki H. Org. Chem. Front. 2022; 9: 1986
• 38a Philippot K, Chaudret B. C. R. Chim. 2003; 6: 1019
• 38b Pery T, Pelzer K, Buntkowsky G, Philippot K, Limbach HH, Chaudret B. ChemPhysChem 2005; 6: 605
• 38c García-Antón J, Axet MR, Jansat S, Philippot K, Chaudret B, Pery T, Buntkowsky G, Limbach HH. Angew. Chem. Int. Ed. 2008; 47: 2074
• 38d Pieters G, Taglang C, Bonnefille E, Gutmann T, Puente C, Berthet JC, Dugave C, Chaudret B, Rousseau B. Angew. Chem. Int. Ed. 2014; 53: 230
• 38e Pfeifer V, Certiat M, Bouzouita D, Palazzolo A, Garcia-Argote S, Marcon E, Buisson DA, Lesot P, Maron L, Chaudret B, Tricard S, Rosal I, Poteau R, Feuillastre S, Pieters G. Chem. Eur. J. 2020; 26: 4988
• 38f Taglang C, Martínez-Prieto LM, del Rosal I, Maron L, Poteau R, Philippot K, Chaudret B, Perato S, Sam Lone A, Puente C, Dugave C, Rousseau B, Pieters G. Angew. Chem. Int. Ed. 2015; 54: 10474
• 38g Bresó-Femenia E, Godard C, Claver C, Chaudret B, Castillón S. Chem. Commun. 2015; 51: 16342
• 38h Palazzolo A, Feuillastre S, Pfeifer V, Garcia-Argote S, Bouzouita D, Tricard S, Chollet C, Marcon E, Buisson DA, Cholet S, Fenaille F, Lippens G, Chaudret B, Pieters G. Angew. Chem. Int. Ed. 2019; 58: 4891
• 38i Pfeifer V, Zeltner T, Fackler C, Kraemer A, Thoma J, Zeller A, Kiesling R. Angew. Chem. Int. Ed. 2021; 60: 26671
• 38j Guy KA, Shapley JR. Organometallics 2009; 28: 4020
• 39a Martínez-Prieto LM, Baquero EA, Pieters G, Flores JC, De Jesús E, Nayral C, Delpech F, van Leeuwen PW. N. M, Lippens G, Chaudret B. Chem. Commun. 2017; 53: 5850
• 39b Suárez-Riaño O, Mencia G, Tricard S, Esvan J, Fazzini P.-F, Chaudret B, Baquero EA. Chem. Commun. 2023; 59: 1062
• 39c Zuluaga-Villamil A, Mencia G, Asensio JM, Fazzini P.-F, Baquero EA, Chaudret B. Organometallics 2022; 41: 3313
• 39d Martinez-Espinar F, Salom-Català A, Bresó-Femenia E, Claver C, Baletto F, Ricart JM, Chaudret B, Carbó JJ, Godard C, Castillon S. Inorg. Chem. 2023; 62: 4570
• 39e Palazzolo A, Naret T, Daniel-Bertrand M, Buisson DA, Tricard S, Lesot P, Coppel Y, Chaudret B, Feuillastre S, Pieters G. Angew. Chem. Int. Ed. 2020; 59: 20879
• 39f Bouzouita D, Asensio JM, Pfeifer V, Palazzolo A, Lecante P, Pieters G, Feuillastre S, Tricard S, Chaudret B. Nanoscale 2020; 12: 15736
• 39g Valero M, Bouzouita D, Palazzolo A, Atzrodt J, Dugave C, Tricard S, Feuillastre S, Pieters G, Chaudret B, Derdau V. Angew. Chem. Int. Ed. 2020; 59: 3517
• 39h Molinillo P, Puyo M, Vattier F, Lacroix B, Rendón N, Lara P, Suárez A. Nanoscale 2023; 15: 14488
• 39i Levernier E, Tatoueix K, Garcia-Argote S, Pfeifer V, Kiesling R, Gravel E, Feuillastre S, Pieters G. JACS Au 2022; 2: 801
• 40a Li W, Rabeah J, Bourriquen F, Yang D, Kreyenschulte C, Rockstroh N, Lund H, Bartling S, Surkus A.-E, Junge K, Brückner A, Lei A, Beller M. Nat. Chem. 2022; 14: 334
• 40b Bourriquen F, Rockstroh N, Bartling S, Junge K, Beller M. Angew. Chem. Int. Ed. 2022; 61: e202202423
• 40c Shao F, Wang K, Jiang W, Xu Z, Li X, Zhong X, Wang J. ACS Catal. 2023; 13: 15746
• 40d Mencia G, Rouan P, Fazzini P.-F, Kulyk H, Varela-Izquierdo V, Lippens G, Chaudret B. Catal. Sci. Technol. 2024; 14: 4904
• 40e Shao F, Ma F, Li Y, Jiang W, Wei Z, Zhong X, Wang H, Wang L, Wang J. ChemSusChem 2023; 16: e202202395
• 40f Jiang W, Shao F, Cheng J, Ma F, Wei Z, Zhong X, Wang H, Wang J. Asian J. Org. Chem. 2023; 12: e202200662

Publication History

Received: 20 September 2024

Accepted after revision: 29 October 2024

Accepted Manuscript online:
04 November 2024

Article published online:
11 December 2024