Catalytic Hydrogen Isotope Exchange Reactions in Late-Stage Functionalization

Qi-Kai Kang; Hang Shi

doi:10.1055/a-1354-0367

Synlett, Table of Contents

Synlett 2022; 33(04): 329-338
DOI: 10.1055/a-1354-0367

cluster

Late-Stage Functionalization

Catalytic Hydrogen Isotope Exchange Reactions in Late-Stage Functionalization

Qi-Kai Kang

^aKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

^bInstitute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

,

Hang Shi∗

^aKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

^bInstitute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

The introduction of deuterium and tritium into molecules is of great importance in drug discovery. Many attempts have been made to develop late-stage hydrogen isotope exchange (HIE) reactions to avoid multistep syntheses using commercially available labeled precursors. In this review, we summarize recent progress in catalytic HIE reactions, with our main focus on their applications in the late-stage labeling of bioactive complex molecules and pharmaceuticals1 Introduction

2 Non-Transition-Metal-Catalyzed Hydrogen Isotope Exchange

2.1 Organocatalysis

2.2 Photoredox Catalysis

3 Transition-Metal-Catalyzed Hydrogen Isotope Exchang

3.1 Palladium

3.2 Ruthenium

3.3 Iridium

3.4 Other Metals

4 Summary

Key words

hydrogen isotope exchange reaction - late-stage functionalization - bioactive molecules - catalytic reaction - C–H functionalization - deuteration - tritiation

Full Text

References

References and Notes
1 Börgel J, Ritter T. Chem 2020; 6: 1877

For selected reviews of late-stage functionalization in drug discovery, see:

2a Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW. Chem. Soc. Rev. 2016; 45: 546
2b Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383
2c Moir M, Danon JJ, Reekie TA, Kassiou M. Expert Opin. Drug Discovery 2019; 14: 1137

For selected reviews of late-stage C–H functionalization, see refs. 2a,b, and:

3a Godula K, Sames D. Science 2006; 312: 67
3b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
3c Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
3d Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2
3e He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
3f Kelly CB, Padilla-Salinas R. Chem. Sci. 2020; 11: 10047
3g Capaldo L, Quadri LL, Ravelli D. Green Chem. 2020; 22: 3376

For selected reviews of deuterium and tritium in drug discovery, see:

4a Gant TG. J. Med. Chem. 2014; 57: 3595
4b Pirali T, Serafini M, Cargnin S, Genazzani AA. J. Med. Chem. 2019; 62: 5276
4c Lockley WJ. S, McEwen A, Cooke R. J. Labelled Compd. Radiopharm. 2012; 55: 235

5 Isin EM, Elmore CS, Nilsson GN, Thompson RA, Weidolf L. Chem. Res. Toxicol. 2012; 25: 532
6 Mullard A. Nat. Rev. Drug Discovery 2017; 16: 305

For previous comprehensive reviews of HIE reaction, see:

7a Junk T, Catallo WJ. Chem. Soc. Rev. 1997; 26: 401
7b Atzrodt J, Derdau V, Fey T, Zimmermann J. Angew. Chem. Int. Ed. 2007; 46: 7744
7c Hesk D, Lavey CF, McNamara P. J. Labelled Compd. Radiopharm. 2010; 53: 722
7d Atzrodt J, Derdau V, Kerr WJ, Reid M. Angew. Chem. Int. Ed. 2018; 57: 3022
7e Valero M, Derdau V. J. Labelled Compd. Radiopharm. 2020; 63: 266

8 Shibasaki H, Furuta T, Kasuya Y. Steroids 1992; 57: 13
9 Wähälä K, Väänänen T, Hase T, Leinonen A. J. Labelled Compd. Radiopharm. 1995; 36: 493
10 Furuta T, Suzuki A, Matsuzawa M, Shibasaki H, Kasuya Y. Steroids 2003; 68: 693
11 Zhan M, Zhang T, Huang H, Xie Y, Chen Y. J. Labelled Compd. Radiopharm. 2014; 57: 533
12 Berthelette C, Scheigetz J. J. Labelled Compd. Radiopharm. 2004; 47: 891
13 Liu M, Chen X, Chen T, Yin S.-F. Org. Biomol. Chem. 2017; 15: 2507
14 Fischer O, Hubert A, Heinrich MR. J. Org. Chem. 2020; 85: 11856
15 Chang Y, Yesilcimen A, Cao M, Zhang Y, Zhang B, Chan JZ, Wasa M. J. Am. Chem. Soc. 2019; 141: 14570
16 Chang Y, Myers T, Wasa M. Adv. Synth. Catal. 2020; 362: 360

For selected reviews on photocatalysis, see:

17a Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
17b Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
17c Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
17d Sideri IK, Voutyritsa E, Kokotos CG. Org. Biomol. Chem. 2018; 16: 4596

18 Loh YY, Nagao KA, Hoover J, Hesk D, Rivera NR, Colletti SL, Davies IW, MacMillan DW. C. Science 2017; 358: 1182
19 Legros F, Fernandez-Rodriguez P, Mishra A, Weck R, Bauer A, Sandvoss M, Ruf S, Méndez M, Mora-Radó H, Rackelmann N, Pöverlein C, Derdau V. Chem. Eur. J. 2020; 26: 12738
20 Dong J, Wang X, Wang Z, Song H, Liu Y, Wang Q. Chem. Sci. 2020; 11: 1026
21 Kuang Y, Cao H, Tang H, Chew J, Chen W, Shi X, Wu J. Chem. Sci. 2020; 11: 8912
22 Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Synlett 2005; 1385

23a Derdau V, Atzrodt J. Synlett 2006; 1918
23b Derdau V, Atzrodt J, Zimmermann J, Kroll C, Brückner F. Chem. Eur. J. 2009; 15: 10397

24 Modutlwa N, Tada H, Sugahara Y, Shiraki K, Hara N, Deyashiki Y, Ando T, Maegawa T, Monguchi Y, Saiiki H. Nucleic Acids Symp. Ser. 2009; 53: 105

25a Zolotarev YA, Dadayan AK, Borisov YA, Kozik VS. Chem. Rev. 2010; 110: 5425
25b Sidorov GV, Myasoedov NF, Lomin SN, Romanov GA. Radiochemistry 2015; 57: 108
25c Shevchenko VP, Nagaev IY, Myasoedov NF. Radiochemistry 2014; 56: 292

26a Gardes GE. E, Pajonk GM, Teichner SJ. J. Catal. 1974; 33: 145
26b Psofogiannakis GM, Froudakis GE. J. Phys. Chem. C 2009; 113: 14908
26c Prins R. Chem. Rev. 2012; 112: 2714
26d Zolotarev YA, Dadayan AK, Borisov YA, Kozik VS, Nazimov IV, Ziganshin RH, Bocharov EV, Chizhov AO, Myasoedov NF. J. Phys. Chem. C 2013; 117: 16878
26e Shevchenko VP, Nagaev IY, Shevchenko KV, Myasoedov NF. Radiochemistry 2013; 55: 346
26f Shevchenko VP, Nagaev IY, Myasoedov NF. Dokl. Chem. 2013; 448: 66
26g Shevchenko VP, Nagaev Y, Yu I, Myasoedov NF. Radiochemistry 2010; 52: 95
26h Zolotarev YA, Firsova YY, Abaimov A, Dadayan AK, Kosik VS, Novikov AV, Krasnov NV, Vaskovskii BV, Nazimov IV, Kovalev GI, Myasoedov NF. Russ. J. Bioorg. Chem. 2009; 35: 296
26i Shevchenko VP, Nagaev IY, Myasoedov NF. Radiochemistry 2009; 51: 175
26j Baitov AA, Sidorov GV, Myasoedov NF. Radiochemistry 2007; 49: 100
26k Shevchenko VP, Nagaev IY, Badun GA, Chernysheva MG, Shevchenko KV, Myasoedov NF. Dokl. Chem. 2012; 442: 42

27 Zolotarev YA, Dadayan AK, Kozik VS, Gasanov EV, Nazimov IV, Ziganshin RK, Vaskovsky BV, Murashov AN, Ksenofontov AL, Kharybin ON, Nikolaev EN, Myasoedov NF. Russ. J. Bioorg. Chem. 2014; 40: 26
28 Sawama Y, Yabe Y, Iwata H, Fujiwara Y, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16436
29 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

30a Pieters G, Taglang C, Bonnefille E, Gutmann T, Puente C, Berthet J, Dugave C, Chaudret B, Rousseau B. Angew. Chem. Int. Ed. 2014; 53: 230
30b Taglang C, Martinez-Prieto LM, del Rosal I, Maron L, Poteau R, Philippot K, Chaudret B, Perato S, Lone AS, Puente C, Dugave C, Rousseau B, Pieters G. Angew. Chem. Int. Ed. 2015; 54: 10474

31 Conley BL, Pennington-Boggio MK, Boz E, Williams TJ. Chem. Rev. 2010; 110: 2294
32 Neubert L, Michalik D, Bahn S, Imm S, Neumann H, Atzrodt J, Derdau V, Holla W, Beller M. J. Am. Chem. Soc. 2012; 134: 12239
33 Chatterjee B, Krishnakumar V, Gunanathan C. Org. Lett. 2016; 18: 5892
34 Müller V, Weck R, Derdau V, Ackermann L. ChemCatChem 2020; 12: 100
35 Hesk D, Das PR, Evans B. J. Labelled Compd. Radiopharm. 1995; 36: 497
36 Shu AY. L, Saunders D, Levinson SH, Landvatter SW, Mahoney A, Senderoff SG, Mack JF, Heys JR. J. Labelled Compd. Radiopharm. 1999; 42: 797
37 Crabtree R. Acc. Chem. Res. 1979; 12: 331

38a Simonsson R, Stenhagen G, Ericsson C, Elmore CS. J. Labelled Compd. Radiopharm. 2013; 56: 334
38b Heys JR, Elmore CS. J. Labelled Compd. Radiopharm. 2009; 52: 189
38c Bushby N, Killick DA. J. Labelled Compd. Radiopharm. 2007; 50: 519
38d Hickey ML. J, Kingston LP, Lockley WJ. S, Allen P, Mather A, Wilkinson DJ. J. Labelled Compd. Radiopharm. 2007; 50: 286
38e Lee HM, Jiang T, Stevens ED, Nolan SP. Organometallics 2001; 20: 1255
38f Vázquez-Serrano LD, Owens BT, Buriak JM. Chem. Commun. 2002; 2518
38g Vazquez-Serrano LD, Owens BT, Buriak JM. Inorg. Chim. Acta 2006; 359: 2786
38h Powell ME, Elmore CS, Dorff PN, Heys JR. J. Labelled Compd. Radiopharm. 2007; 50: 523
38i Parmentier M, Hartung T, Pfaltz A, Muri D. Chem. Eur. J. 2014; 20: 11496
38j Burhop A, Prohaska R, Weck R, Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2017; 60: 343
38k Valero M, Mishra A, Blass J, Weck R, Derdau V. ChemistryOpen 2019; 8: 1183
38l Valero M, Kruissink T, Blass J, Weck R, Güssregen S, Plowright AT, Derdau V. Angew. Chem. Int. Ed. 2020; 59: 5626

39a Kerr WJ, Knox GJ, Paterson LC. J. Labelled Compd. Radiopharm. 2020; 63: 281
39b Cochrane AR, Idziak C, Kerr WJ, Mondal B, Paterson LC, Tuttle T, Andersson S, Nilsson GN. Org. Biomol. Chem. 2014; 12: 3598
39c Kerr WJ, Lindsay DM, Reid M, Atzrodt J, Derdau V, Rojahn P, Weck R. Chem. Commun. 2016; 52: 6669
39d Kerr WJ, Reid M, Tuttle T. ACS Catal. 2015; 5: 402
39e For a bidentate Ir(I)-NHC-P-complex-catalyzed HIE of molecules bearing a sulfone motif, see: Kerr WJ, Knox GJ, Reid M, Tuttle T, Bergare J, Bragg RA. ACS Catal. 2020; 10: 11120

40a Burhop A, Weck R, Atzrodt J, Derdau V. Eur. J. Org. Chem. 2017; 1418
40b Valero M, Becker D, Jess K, Weck R, Atzrodt J, Bannenberg T, Derdau V, Tamm M. Chem. Eur. J. 2019; 25: 6517
40c Jess K, Derdau V, Weck R, Atzrodt J, Freytag M, Jones PG, Tamm M. Adv. Synth. Catal. 2017; 359: 629
40d 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
40e Daniel-Bertrand M, Garcia-Argote S, Palazzolo A, Marin IM, Fazzini P.-F, Tricard S, Chaudret B, Derdau V, Feuillastre S, Pieters G. Angew. Chem. Int. Ed. 2020; 59: 21114

41a Kerr WJ, Mudd RJ, Reid M, Atzrodt J, Derdau V. ACS Catal. 2018; 8: 10895
41b Valero M, Weck R, Ggssregen S, Atzrodt J, Derdau V. Angew. Chem. Int. Ed. 2018; 57: 8159

42 Zhou J, Hartwig JF. Angew. Chem. Int. Ed. 2008; 47: 5783
43 Yu RP, Hesk D, Rivera N, Pelczer I, Chirik PJ. Nature 2016; 529: 195
44 Yu RP, Darmon JM, Semproni SP, Turner ZR, Chirik PJ. Organometallics 2017; 36: 4341

45a Yang H, Zarate C, Palmer WN, Rivera N, Hesk D, Chirik PJ. ACS Catal. 2018; 8: 10210
45b Zarate C, Yang H, Bezdek MJ, Hesk D, Chirik PJ. J. Am. Chem. Soc. 2019; 141: 5034