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Synlett 2022; 33(04): 329-338
DOI: 10.1055/a-1354-0367
DOI: 10.1055/a-1354-0367
cluster
Late-Stage Functionalization
Catalytic Hydrogen Isotope Exchange Reactions in Late-Stage Functionalization
This project was supported by the National Natural Science Foundation of China (22071198) and the China Postdoctoral Science Foundation (2019M662118)
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 - tritiationPublication History
Received: 16 November 2020
Accepted after revision: 14 January 2021
Accepted Manuscript online:
14 January 2021
Article published online:
08 February 2021
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References and Notes
- 1 Börgel J, Ritter T. Chem 2020; 6: 1877
- 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
- 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
- 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
- 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
- 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
For selected reviews of late-stage functionalization in drug discovery, see:
For selected reviews of late-stage C–H functionalization, see refs. 2a,b, and:
For selected reviews of deuterium and tritium in drug discovery, see:
For previous comprehensive reviews of HIE reaction, see:
For selected reviews on photocatalysis, see: