2.13 Base-Metal-Catalyzed Hydrogenation of Polar Unsaturated Bonds
Book
Editor: Yoshikai, N.
Title: Base-Metal Catalysis 2
Print ISBN: 9783132455030; Online ISBN: 9783132455054; Book DOI: 10.1055/b000000440
1st edition © 2023 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract

The catalytic hydrogenation of carbonyl compounds to afford the corresponding saturated products is of great significance in both organic synthesis and industrial application. Historically, such transformations have generally been based on the use of noble-metal catalysts; however, in recent years, much attention has been paid to the development of earth-abundant-metal catalysts as alternatives to the well-established noble-metal congeners in terms of sustainability. This review comprehensively describes the hydrogenation of carbonyl compounds and related functional groups catalyzed by base metals, including iron, cobalt, manganese, nickel, and copper. These results are expected to promote the further development and prosperity of base-metal catalysis.
Key words
base-metal catalysis - hydrogenation - asymmetric hydrogenation - carbonyl compounds - imines - nitriles - heteroarenes - iron - cobalt - manganese - nickel - copper- 14 Rautenstrauch V, Hoang-Cong X, Churlaud R, Abdur-Rashid K, Morris RH. Chem.–Eur. J. 2003; 9: 4954
- 16 Kuriyama W, Matsumoto T, Ogata O, Ino Y, Aoki K, Tanaka S, Ishida K, Kobayashi T, Sayo N, Saito T. Org. Process Res. Dev. 2012; 16: 166
- 29 Llopis Q, Ayad T, Phansavath P, Ratovelomanana-Vidal V. Science of Synthesis: Catalytic Reduction in Organic Synthesis 2018; 2: 93
- 32 Abdur-Rashid K, Clapham SE, Hadzovic A, Harvey JN, Lough AJ, Morris RH. J. Am. Chem. Soc. 2002; 124: 15104
- 50 Elangovan S, Topf C, Fischer S, Jiao H, Spannenberg A, Baumann W, Ludwig R, Junge K, Beller M. J. Am. Chem. Soc. 2016; 138: 8809
- 53 Langer R, Iron MA, Konstantinovski L, Diskin-Posner Y, Leitus G, Ben-David Y, Milstein D. Chem.–Eur. J. 2012; 18: 7196
- 57 Chakraborty S, Lagaditis PO, Förster M, Bielinski EA, Hazari N, Holthausen MC, Jones WD, Schneider S. ACS Catal. 2014; 4: 3994
- 58 Gorgas N, Stöger B, Veiros LF, Pittenauer E, Allmaier G, Kirchner K. Organometallics 2014; 33: 6905
- 63 Facchini SV, Neudörfl J.-M, Pignataro L, Cettolin M, Gennari C, Berkessel A, Piarulli U. ChemCatChem 2017; 9: 1461
- 64 Weber S, Brünig J, Zeindlhofer V, Schröder C, Stöger B, Limbeck A, Kirchner K, Bica K. ChemCatChem 2018; 10: 4386
- 67 Gärtner D, Welther A, Rad BR, Wolf R, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2014; 53: 3722
- 70 Duan Y.-N, Du X, Cui Z, Zeng Y, Liu Y, Yang T, Wen J, Zhang X. J. Am. Chem. Soc. 2019; 141: 20424
- 75 Li H, Wei D, Bruneau-Voisine A, Ducamp M, Henrion M, Roisnel T, Dorcet V, Darcel C, Carpentier J.-F, Soulé J.-F, Sortais J.-B. Organometallics 2018; 37: 1271
- 76 Wei D, Bruneau-Voisine A, Chauvin T, Dorcet V, Roisnel T, Valyaev DA, Lugan N, Sortais J.-B. Adv. Synth. Catal. 2018; 360: 676
- 78 Buhaibeh R, Filippov OA, Bruneau-Voisine A, Willot J, Duhayon C, Valyaev DA, Lugan N, Canac Y, Sortais J.-B. Angew. Chem. Int. Ed. 2019; 58: 6727
- 81 Yang W, Chernyshov IY, van Schendel RKA, Weber M, Müller C, Filonenko GA, Pidko EA. Nat. Commun. 2021; 12: 12
- 86 Sui-Seng C, Haque FN, Hadzovic A, Pütz A.-M, Reuss V, Meyer N, Lough AJ, Zimmer-De Iuliis M, Morris RH. Inorg. Chem. 2009; 48: 735
- 89 Lagaditis PO, Sues PE, Sonnenberg JF, Wan KY, Lough AJ, Morris RH. J. Am. Chem. Soc. 2014; 136: 1367
- 91 Sonnenberg JF, Lough AJ, Morris RH. Organometallics 2014; 33: 6452 Organometallics 2016; 35: 2772
-
92 Gajewski P, Renom-Carrasco M, Facchini SV, Pignataro L, Lefort L, de Vries JG, Ferraccioli R, Forni A, Piarulli U, Gennari C. Eur. J. Org. Chem. 2015; 1887
- 94 Zirakzadeh A, Kirchner K, Roller A, Stöger B, Widhalm M, Morris RH. Organometallics 2016; 35: 3781
- 99 Widegren MB, Harkness GJ, Slawin AMZ, Cordes DB, Clarke ML. Angew. Chem. Int. Ed. 2017; 56: 5825 Angew. Chem. Int. Ed. 2017; 56: 9265
- 100 Garbe M, Junge K, Walker S, Wei Z, Jiao H, Spannenberg A, Bachmann S, Scalone M, Beller M. Angew. Chem. Int. Ed. 2017; 56: 11237
- 110 Deng C.-Q, Liu J, Luo J.-H, Gan L.-J, Deng J, Fu Y. Angew. Chem. Int. Ed. 2022; 61: e202 115 983
- 113 Shimizu H, Igarashi D, Kuriyama W, Yusa Y, Sayo N, Saito T. Org. Lett. 2007; 9: 1655 Org. Lett. 2007; 9: 3199
- 115 Krabbe SW, Hatcher MA, Bowman RK, Mitchell MB, McClure MS, Johnson JS. Org. Lett. 2013; 15: 4560
- 116 Zatolochnaya OV, Rodríguez S, Zhang Y, Lao KS, Tcyrulnikov S, Li G, Wang X.-J, Qu B, Biswas S, Mangunuru HPR, Rivalti D, Sieber JD, Desrosiers J.-N, Leung JC, Grinberg N, Lee H, Haddad N, Yee NK, Song JJ, Kozlowski MC, Senanayake CH. Chem. Sci. 2018; 9: 4505
- 121 Werkmeister S, Junge K, Wendt B, Alberico E, Jiao H, Baumann W, Junge H, Gallou F, Beller M. Angew. Chem. Int. Ed. 2014; 53: 8722
- 122 Chakraborty S, Dai H, Bhattacharya P, Fairweather NT, Gibson MS, Krause JA, Guan H. J. Am. Chem. Soc. 2014; 136: 7869
- 123 Elangovan S, Wendt B, Topf C, Bachmann S, Scalone M, Spannenberg A, Jiao H, Baumann W, Junge K, Beller M. Adv. Synth. Catal. 2016; 358: 820
- 124 Gajewski P, Gonzalez-de-Castro A, Renom-Carrasco M, Piarulli U, Gennari C, de Vries JG, Lefort L, Pignataro L. ChemCatChem 2016; 8: 3431
- 125 Srimani D, Mukherjee A, Goldberg AF, Leitus G, Diskin-Posner Y, Shimon LJW, Ben-David Y, Milstein D. Angew. Chem. Int. Ed. 2015; 54: 12357
- 127 Junge K, Wendt B, Cingolani A, Spannenberg A, Wei Z, Jiao H, Beller M. Chem.–Eur. J. 2018; 24: 1046
- 128 Elangovan S, Garbe M, Jiao H, Spannenberg A, Junge K, Beller M. Angew. Chem. Int. Ed. 2016; 55: 15364
- 129 Espinosa-Jalapa NA, Nerush A, Shimon LJW, Leitus G, Avram L, Ben-David Y, Milstein D. Chem.–Eur. J. 2017; 23: 5934
- 130 van Putten R, Uslamin EA, Garbe M, Liu C, Gonzalez-de-Castro A, Lutz M, Junge K, Hensen EJM, Beller M, Lefort L, Pidko EA. Angew. Chem. Int. Ed. 2017; 56: 7531
- 132 Yang W, Kalavalapalli TY, Krieger AM, Khvorost TA, Chernyshov IY, Weber M, Uslamin EA, Pidko EA, Filonenko GA. J. Am. Chem. Soc. 2022; 144: 8129
- 133 Zimmermann BM, Ngoc TT, Tzaras D.-I, Kaicharla T, Teichert JF. J. Am. Chem. Soc. 2021; 143: 16865
- 138 Papa V, Cabrero-Antonino JR, Alberico E, Spanneberg A, Junge K, Junge H, Beller M. Chem. Sci. 2017; 8: 3576
- 141 Zou Y.-Q, Chakraborty S, Nerush A, Oren D, Diskin-Posner Y, Ben-David Y, Milstein D. ACS Catal. 2018; 8: 8014
- 142 Papa V, Cabrero-Antonino JR, Spannenberg A, Junge K, Beller M. Catal. Sci. Technol. 2020; 10: 6116
- 146 Zubar V, Lebedev Y, Azofra LM, Cavallo L, El-Sepelgy O, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 13439
- 147 Ferretti F, Scharnagl FK, DallʼAnese A, Jackstell R, Dastgir S, Beller M. Catal. Sci. Technol. 2019; 9: 3548
- 149 Korstanje TJ, van der Vlugt JI, Elsevier CJ, de Bruin B. Science (Washington, D. C.) 2015; 350: 298
- 150 Langer R, Diskin-Posner Y, Leitus G, Shimon LJW, Ben-David Y, Milstein D. Angew. Chem. Int. Ed. 2011; 50: 9948
- 151 Rivada-Wheelaghan O, Dauth A, Leitus G, Diskin-Posner Y, Milstein D. Inorg. Chem. 2015; 54: 4526
- 152 Zhang Y, MacIntosh AD, Wong JL, Bielinski EA, Williard PG, Mercado BQ, Hazari N, Bernskoetter WH. Chem. Sci. 2015; 6: 4291
- 154 Bertini F, Gorgas N, Stöger B, Peruzzini M, Veiros LF, Kirchner K, Gonsalvi L. ACS Catal. 2016; 6: 2889
- 156 Badiei YM, Wang W.-H, Hull JF, Szalda DJ, Muckerman JT, Himeda Y, Fujita E. Inorg. Chem. 2013; 52: 12576
- 160 Vollmer MV, Ye J, Linehan JC, Graziano BJ, Preston A, Wiedner ES, Lu CC. ACS Catal. 2020; 10: 2459
- 162 Bertini F, Glatz M, Gorgas N, Stöger B, Peruzzini M, Veiros LF, Kirchner K, Gonsalvi L. Chem. Sci. 2017; 8: 5024
- 164 Cammarota RC, Vollmer MV, Xie J, Ye J, Linehan JC, Burgess SA, Appel AM, Gagliardi L, Lu CC. J. Am. Chem. Soc. 2017; 139: 14244
- 166 Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9777
- 167 Ziebart C, Federsel C, Anbarasan P, Jackstell R, Baumann W, Spannenberg A, Beller M. J. Am. Chem. Soc. 2012; 134: 20701
- 169 Daw P, Chakraborty S, Leitus G, Diskin-Posner Y, Ben-David Y, Milstein D. ACS Catal. 2017; 7: 2500
- 172 Dong K, Elangovan S, Sang R, Spannenberg A, Jackstell R, Junge K, Li Y, Beller M. Nat. Commun. 2016; 7: 12075
- 175 Pagnoux-Ozherelyeva A, Pannetier N, Mbaye MD, Gaillard S, Renaud J.-L. Angew. Chem. Int. Ed. 2012; 51: 4976
- 177 Sandl S, Maier TM, van Leest NP, Kröncke S, Chakraborty U, Demeshko S, Koszinowski K, de Bruin B, Meyer F, Bodensteiner M, Herrmann C, Wolf R, Jacobi von Wangelin A. ACS Catal. 2019; 9: 7596
- 178 Wei D, Bruneau-Voisine A, Valyaev DA, Lugan N, Sortais J.-B. Chem. Commun. (Cambridge) 2018; 54: 4302
- 189 Bornschein C, Werkmeister S, Wendt B, Jiao H, Alberico E, Baumann W, Junge H, Junge K, Beller M. Nat. Commun. 2014; 5: 4111
- 191 Lange S, Elangovan S, Cordes C, Spannenberg A, Jiao H, Junge H, Bachmann S, Scalone M, Topf C, Junge K, Beller M. Catal. Sci. Technol. 2016; 6: 4768
- 192 Mukherjee A, Srimani D, Chakraborty S, Ben-David Y, Milstein D. J. Am. Chem. Soc. 2015; 137: 8888
- 193 Adam R, Bheeter CB, Cabrero-Antonino JR, Junge K, Jackstell R, Beller M. ChemSusChem 2017; 10: 842