Photo- and electro-catalytic deuteration of feedstock chemicals and pharmaceuticals: A review

doi:10.1016/S1872-2067(21)63928-1

Abstract

Abstract:

Deuterium labeling techniques are widely utilized as efficient tools to study the absorption, distribution, metabolism, and excretion (ADME) of pharmaceuticals. Moreover, deuterium-labeled drugs are expected to prolong the half-life of drug metabolism, enhance the efficacy of drugs, close metabolic sites, and decrease side effects. Thus, there is a rising demand for the practical construction of deuterium-labeled drugs and their intermediates under mild conditions. This paper timely provides an overview of the recent advances in both photo- and electro-catalytic mild and selective deuteration of fine chemicals and pharmaceuticals with low-cost and sustainable deuterium source. Three types of deuteration strategies are discussed according to the deuteration mode, named deuterium atom transfer strategy, deuterium atom abstraction strategy and deuterated water splitting strategy respectively. The application scope and mechanistic insights are discussed comprehensively. Finally, the perspective on the challenges and future development trends for photo- and electro-catalytic deuteration strategies are also presented.

Key words: Photocatalysis, Electrocatalysis, Deuterium-labelled drugs, H/D atom transfer, Single electron transfer

Wei Ou, Chuntian Qiu, Chenliang Su. Photo- and electro-catalytic deuteration of feedstock chemicals and pharmaceuticals: A review[J]. Chinese Journal of Catalysis, 2022, 43(4): 956-970.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63928-1

https://www.cjcatal.com/EN/Y2022/V43/I4/956

Figures/Tables 30

Fig. 1. Photo- and electro-catalytic deuteration of fine chemicals and pharmaceuticals.

Scheme 1. Photocatalytic DAT strategy for the deuterium labeling of organic molecules.

Scheme 2. Photocatalytic decarboxylative deuteration of free carboxylic acids.

Scheme 3. Photocatalytic deoxygenative deuteration of carboxylic acids.

Scheme 4. Photocatalytic desulfurization-deuteration reactions.

Scheme 5. Photocatalytic radical deuteroamidation of various alkenes.

Scheme 6. Photocatalytic deuterodehalogenation of aryl and alkyl chlorides.

Scheme 7. Photocatalytic deuteration of alkyl halides using the XAT protocol.

Scheme 8. Incorporation of deuterium at α-amino sp3C-H bonds by photocatalysis.

Scheme 9. Photocatalytic deuteration of amino acids and peptides.

Scheme 10. Selective photocatalytic deuteration of formyl C-H and hydridic C(sp3)-H bonds.

Scheme 11. Photocatalytic deuteration of formyl groups.

Scheme 13. Photo/electrocatalytic deuterium atom abstraction from solvent by radicals.

Scheme 14. Photocatalytic decarboxylative deuteration of carboxylic acid esters.

Scheme 15. Photocatalytic dehalogenative deuteration of inactivated aryl and alkyl halides with a palladium complex.

Scheme 16. Visible-light-driven deutero-deamination of anilines.

Scheme 17. Direct electrochemical reductive amination using DMSO-d6 as the deuterium source.

Scheme 18. Photo/electrocatalytic deuterium abstraction from D2O by carbanions.

Scheme 19. Synthesis of asymmetric α-deuterated α-amino acids.

Scheme 20. Ketimine reduction for the synthesis of α-deuterated amines using Cy2NMe and D2O.

Scheme 21. Photoredox-catalyzed enantioselective α-deuteration of aza-arenes with D2O.

Scheme 22. Electrochemical deuteration of α,β-unsaturated carbonyl compounds.

Scheme 23. Heavy water splitting strategy for the synthesis of deuterium-labeled compounds.

Scheme 24. Photocatalytic heavy water splitting for the deuteration of halides.

Scheme 26. Dehalogenative deuteration of halides by electrocatalysis.

Scheme 28. Photocatalytic N-trideuteromethylation of amines.

References

[1]	W. J. S. Lockley, A. McEwen, R. Cooke, Tritium, J. Labelled Compd. Radiopharm., 2012, 55, 235-257.
[2]	P. H. Allen, M. J. Hickey, L. P. Kingston, D. J. Wilkinson, J. Labelled Compd. Radiopharm., 2010, 53, 731-738.
[3]	C. S. Elmore, R. A. Bragg, Bioorg. Med. Chem. Lett., 2015, 25, 167-171.
[4]	C. S. Elmore, Annu. Rep. Med. Chem., 2009, 44, 515-534.
[5]	V. Derdau, J. Atzrodt, J. Zimmermann, C. Kroll, F. Brückner, Chem. Eur. J., 2009, 15, 10397-10404.
[6]	A. Katsnelson, Nat. Med., 2013, 19, 656.
[7]	E. M. Isin, C. S. Elmore, G. N. Nilsson, R. A. Thompson, L. Weidolf, Chem. Res. Toxicol., 2012, 25, 532-542.
[8]	B. Belleau, J. Burba, M. Pindell, J. Reiffenstein, Science, 1961, 133, 102-104.
[9]	C. Schmidt, Nat. Biotechnol., 2017, 35, 493-494.
[10]	Y. Zhang, Prog. Pharm. Sci., 2017, 41, 902-918.
[11]	J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed., 2007, 46, 7744-7765
[12]	J. Atzrodt, V. Derdau, W. J. Kerr, M. Reid, Angew. Chem. Int. Ed., 2018, 57, 3022-3047
[13]	T. Junk, W. J. Catallo, Chem. Soc. Rev., 1997, 26, 401-406.
[14]	A. Burhop, R. Prohaska, R. Weck, J. Atzrodt, V. Derdau, J. Labelled Compd. Radiopharm., 2017, 60, 343-348.
[15]	Y. Sawama, Y. Monguchi, H. Sajiki, Synlett, 2012, 23, 959-972.
[16]	R. P. Yu, D. Hesk, N. Rivera, I. Pelczer, P. J. Chirik, Nature, 2016, 529, 195-199.
[17]	J. J. Verendel, O. Pamies, M. Dieguez, P. G. Andersson, Chem. Rev., 2014, 114, 2130-2169.
[18]	R. H. Crabtree, Acc. Chem. Res., 1979, 12, 331-337.
[19]	P. W. C. Cross, J. M. Herbert, W. J. Kerr, A. H. McNeill, L. C. Paterson, Synlett, 2016, 27, 111-115
[20]	J. A. Brown, S. Irvine, A. R. Kennedy, W. J. Kerr, S. Andersson, G. N. Nilsson, Chem. Commun., 2008, 1115-1118.
[21]	G. Zhang, W. Ou, J. Wang, Y. Xu, D. Xu, T. Sun, S. Xiao, M. Wang, H. Li, W. Chen, C. Su, Appl. Catal. B, 2019, 245, 114-121.
[22]	W. Ou, Y. Xu, H. Zhou, C. Su, Sol. RRL, 2021, 5, 2000444.
[23]	T. Sun, G. Zhang, D. Xu, X. Lian, H. Li, W. Chen, C. Su, Mater. Today Energy, 2019, 12, 215-238.
[24]	H. Sun, Y. Ma, Q. Zhang, C. Su, Trans. Tianjin Univ., 2021, 27, 313-330.
[25]	F. Yu, L. C. Wang, Q. J. Xing, D. Wang, X. Jiang, G. Li, A. Zheng, F. Ai, J.-P. Zou, Chin. Chem. Lett., 2020, 31, 1648-1653.
[26]	X. Y. Yu, J. R. Chen, W.-J. Xiao, Chem. Rev., 2021, 121, 506-561.
[27]	F. Lian, K. Xu, Chin. J. Org. Chem., 2020, 40, 3490-3491.
[28]	J. Luo, W. Zhang, H. Yang, Q. Fan, F. Xiong, S. Liu, D.-S. Li, B. Liu, EcoMat, 2021, 3, e12079. 
[29]	L. Buzzetti, G. E. M. Crisenza, P. Melchiorre, Angew. Chem. Int. Ed., 2019, 58, 3730-3747.
[30]	H. Cao, X. Tang, H. Tang, Y. Yuan, J. Wu, Chem. Catal., 2021, 1, 523-598.
[31]	P. Ranjan, S. Pillitteri, E. V. V. Eycken, U. K. Sharma, Green Chem., 2020, 22, 7725-7736.
[32]	R. Zhou, L. Ma, X. Yang, J. Cao, Org. Chem. Front., 2021, 8, 426-444.
[33]	F. Strieth-Kalthoff, M. J. James, M. Teders, L. Pitzer, F. Glorius, Chem. Soc. Rev., 2018, 47, 7190-7202.
[34]	J. Xuan, Z. G. Zhang, W. J. Xiao, Angew. Chem. Int. Ed., 2015, 54, 15632-15641.
[35]	H. Huang, K. Jia, Y. Chen, ACS Catal., 2016, 6, 4983-4988.
[36]	T. Itou, Y. Yoshimi, K. Nishikaw, T. Morita, Y. Okada, N. Ichinosec, M. Hatanaka, Chem. Commun., 2010, 46, 6177-6179.
[37]	J. D. Griffin, M. A. Zeller, D. A. Nicewicz, J. Am. Chem. Soc., 2015, 137, 11340-11348.
[38]	E. E. Stache, A. B. Ertel, T. Rovis, A. G. Doyle, ACS Catal., 2018, 8, 11134-11139.
[39]	M. Zhang, X. A. Yuan, C. Zhu, J. Xie, Angew. Chem. Int. Ed., 2019, 58, 312-316.
[40]	S. Shi, R. Li, L. Rao, Z. Sun, Green Chem., 2020, 22, 669-672.
[41]	L. McMurray, T, M. McGuire, R. L. Howells, Synthesis, 2020, 52, 1719-1737.
[42]	H. Jiang, A. Studer, Chem. Eur. J., 2019, 25, 7105-7109.
[43]	Y. Li, Z. Ye, Y. Lin, Y. Liu, Y. Zhang, L. Gong, Nat. Commun., 2021, 12, 2894.
[44]	T. Constantin, M. Zanini, A. Regni, N. S. Sheikh, F. Juliá, D. Leonori, Science, 2020, 367, 1021-1026.
[45]	Y. Y. Loh, K. Nagao, A. J. Hoover, D. Hesk, N. R. Rivera, S. L. Colletti, I. W. Davies, D. W. C. MacMillan, Science, 2017, 358, 1182-1187.
[46]	B. Zilate, C. Fischer, L. Schneider, C. Sparr, Synthesis, 2019, 51, 4359-4366.
[47]	F. Legros, P. Fernandez-Rodriguez, A. Mishra, R. Weck, A. Bauer, M. Sandvoss, S. Ruf, M. Mendez, H. Mora-Radj, N. Rackelmann, C. Pcverlein, V. Derdau, Chem. Eur. J., 2020, 26, 12738-12742.
[48]	E. C. Gentry, R. R. Knowles, Acc. Chem. Res., 2016, 49, 1546-1556.
[49]	J. Dong, X. Wang, Z. Wang, H. Song, Y. Liu, Q. Wang, Chem. Sci., 2020, 11, 1026-1031.
[50]	Y. Kuang, H. Cao, H. Tang, J. Chew, W. Chen, X. Shi, J. Wu, Chem. Sci., 2020, 11, 8912-8918.
[51]	Y. hang, P. Ji, Y. Dong, Y. Wei, W. Wang, ACS Catal., 2020, 10, 2226-2230.
[52]	J. Y. Dong, W. T. Xu, F. Y. Yue, H. J. Song, Y. X. Liu, Q. M. Wang, Tetrahedron, 2021, 82, 131946.
[53]	X. Y. Du, Z. Huang, ACS Catal., 2017, 7, 1227-1243.
[54]	R. Zhou, J. Li, H. W. Cheo, R. Chua, G. Zhan, Z. Hou, J. Wu, Chem. Sci., 2019, 10, 7340-7344.
[55]	T. Patra, S. Mukherjee, J. Ma, F. Strieth-Kalthoff, F. Glorius, Angew. Chem. Int. Ed., 2019, 58, 10514-10520.
[56]	C. Liu, Z. Chen, C. Su, X. Zhao, Q. Gao, G. H. Ning, H. Zhu, W. Tang, K. Leng, W. Fu, B. Tian, X. Peng, J. Li, Q. H. Xu, W. Zhou, K. P. Loh, Nat. Commun., 2018, 9, 80.
[57]	I. Ghosh, T. Ghosh, J. I. Bardagi, B. König, Science, 2014, 346, 725-728.
[58]	J. D. Nguyen, E. M. DAmato, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem., 2012, 4, 854-859.
[59]	W. Ou, R. Zou, M. Han, L. Yu, C. Su, Chin. Chem. Lett., 2020, 31, 67-70.
[60]	Z. Z. Zhou, J. H. Zhao, X. Y. Gou, X.-M. Chen, Y. M. Liang, Org. Chem. Front., 2019, 6, 1649-1654.
[61]	M. Majek, F. Filace, A. J. Wangelin, Chem. Eur. J., 2015, 21, 4518-4522.
[62]	H. I. M. Amin, C. Raviola, A. A. Amin, B. Mannucci, S. Protti, M. Fagnoni, Molecules, 2019, 24, 2164.
[63]	H. Hong, Z. Zou, G. Liang, S. Pu, J. Hu, L. Chen, Z. Zhu, Y. Li, Y. Huang, Org. Biomol. Chem., 2020, 18, 5832-5837.
[64]	P. Ji, Y. Zhang, Y. Dong, H. Huang, Y. Wei, W. Wang, Org. Lett., 2020, 22, 1557-1562.
[65]	N. X. Xu, B. X. Li, C. Wang, M. Uchiyama, Angew. Chem. Int. Ed., 2020, 59, 10639-10644.
[66]	W. Liu, X. Zheng, J. Zeng, P. Cheng, Chin. J. Org. Chem., 2017, 37, 1-19.
[67]	J. Rong, P. H. Seeberger, K. Gilmore, Org. Lett., 2018, 20, 4081-4085.
[68]	Y. C. Liu, X. Zheng, P. Q. Huang, Acta Chim. Sin, 2019, 77, 850-855.
[69]	R. Wang, M. Ma, X. Gong, G. B. Panetti, X. Fan, P. J. Walsh, Org. Lett., 2018, 20, 2433-2436.
[70]	R. Brimioulle, D. Lenhart, M. M. Maturi, T. Bach, Angew. Chem. Int. Ed., 2015, 54, 3872-3890.
[71]	T. Shao, Y. Li, N. Ma, C. Li, G. Chai, X. Zhao, B. Qiao, Z. Jiang, iScience, 2019, 16, 410-419.
[72]	X. Liu, R. Liu, J. Qiu, X. Cheng, G. Li, Angew. Chem. Int. Ed., 2020, 59, 13962-13967.
[73]	H. Chen, H. K. Mulmudi, A. Tricoli, Chin. Chem. Lett., 2020, 31, 601-604.
[74]	F. Yu, L. Wang, Q. Xing, D. Wang, X. Jiang, G. Li, A. Zheng, F. Ai, J.-P. Zou, Chin. Chem. Lett., 2020, 31, 1648-1653.
[75]	Y. Tong, H. Liu, M. Dai, L. Xiao, X. Wu, Chin. Chem. Lett., 2020, 31, 2295-2299.
[76]	Y. Xu, C. Qiu, X. Fan, Y. Xiao, G. Zhang, K. Yu, H. Ju, X. Ling, Y. Zhu, C. Su, Appl. Catal. B, 2020, 268, 118457.
[77]	X. Fan, Y. Yao, Y. Xu, L. Yu, C. Qiu, ChemCatChem, 2019, 11, 2596-2599.
[78]	C. Qiu, Y. Sun, Y. Xu, B. Zhang, X. Zhang, L. Yu, C. Su, ChemSusChem, 2021, 14, 3344-3350.
[79]	X. Ling, Y. Xu, S. Wu, M. Liu, P. Yang, C. Qiu, G. Zhang, H. Zhou, C. Su, Sci. China Chem., 2020, 63, 386-392.
[80]	Y. Dong, Y. Su, L. Du, R. Wang, L. Zhang, D. Zhao, W. Xie, ACS Nano, 2019, 13, 10754-10760.
[81]	X. L. Nan, Y. Wang, X. B. Li, C. H. Tung, L. Z. Wu, Chem. Commun., 2021, 57, 6768-6771.
[82]	B. Zhang, C. Qiu, S. Wang, H. Gao, K. Yu, Z. Zhang, X. Ling, W. Ou, C. Su, Sci. Bull., 2021, 66, 562-569.
[83]	C. Liu, S. Han, M. Li, X. Chong, B. Zhang, Angew. Chem. Int. Ed., 2020, 59, 18527-18531.
[84]	L. Lu, H. Li, Y. Zheng, F. Bu, A. Lei, CCS Chem., 2020, 2, 2669-2675.
[85]	C. Qiu, Y. Xu, X. Fan, D. Xu, R. Tandiana, X. Ling, Y. Jiang, C. Liu, L. Yu, W. Chen, C. Su, Adv. Sci., 2019, 6, 1801403.
[86]	A. Kurimoto, R. S. Sherbo, Y. Cao, N. W. X. Loo, C. P. Berlinguette, Nat. Catal., 2020, 3, 719-726.
[87]	Y. Wu, C. Liu, C. Wang, S. Lu, B. Zhang, Angew. Chem. Int. Ed., 2020, 59, 21170-21175.
[88]	Z. Zhang, C. Qiu, Y. Xu, Q. Han, J. Tang, K. P. Loh, C. Su, Nat. Commun., 2020, 11, 4722.
[89]	I. M. Mandity, T. A. Martinek, F. Darvas, F. Fülöp, Tetrahedron Lett., 2009, 50, 4372-4374.
[90]	E. R. M. Habraken, P. Haspeslagh, M. Vliegen, T. Noël, J. Flow Chem., 2015, 5, 2-5.
[91]	S. Bhatia, G. Spahlinger, N. Boukhumseen, Q. Boll, Z. Li, J. E. Jackson, Eur. J. Org. Chem., 2016, 2016, 4230-4235.
[92]	W. Ou, X. Xiang, R. Zou, Q. Xu, K. P. Loh, C. Su, Angew. Chem. Int. Ed., 2021, 60, 6357-6361.
[93]	W. Ou, F. Han, X.-N. Hu, H. Chen, P.-Q. Huang, Angew. Chem. Int. Ed., 2018, 57, 11354-11358.
[94]	Z. Liu, X. Nan, T. Lei, C. Zhou, Y. Wang, W. Liu, B. Chen, C. Tung, L. Wu, Chin. J. Catal., 2018, 39, 487-494.
[95]	M. Gupta, S. Paul, R. Gupta, Chin. J. Catal., 2014, 35, 444-450.
[96]	A. Shiri, F. Soleymanpour, H. Eshghi, I. Khosravi, Chin. J. Catal., 2015, 36, 1191-1196.
[97]	Z. Wei, J. Liu, W. Shangguan, Chin. J. Catal., 2020, 41, 1440-1450.
[98]	C. Li, Y. Ma, H. Liu, L. Tao, Y. Ren, X. Chen, H. Li, Q. Yang, Chin. J. Catal., 2020, 41, 1288-1297.
[99]	K. Khan, L. Xu, M. Shi, J. Qu, X. Tao, Z. Feng, C. Li, R. Li, Chin. J. Catal., 2021, 42, 1004-1012.
[100]	R. Li, Chin. J. Catal., 2017, 38, 5-12.
[101]	R. W. Pipal, K. T. Stout, P. Z. Musacchio, S. Ren, T. J. A. Graham,. S. Verhoog, L. Gantert, T. G. Lohith, A. Schmitz, H. S. Lee, D. Hesk, E. D. Hostetler, I. W. Davies, D. W. C. MacMillan, Nature, 2021, 589, 542-547.