光、电催化合成氘代化学品和药物分子研究综述

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

催化学报 ›› 2022, Vol. 43 ›› Issue (4): 956-970.DOI: 10.1016/S1872-2067(21)63928-1

光、电催化合成氘代化学品和药物分子研究综述

欧伟, 邱春天^*(), 苏陈良^#()

深圳大学光电子工程学院, 微纳光电子学研究院, 教育部二维材料光电科技国际合作联合实验室, 广东深圳518060

收稿日期:2021-07-20 接受日期:2021-07-20 出版日期:2022-03-05 发布日期:2021-09-06
通讯作者: 邱春天,苏陈良
基金资助:
国家自然科学基金(21972094);国家自然科学基金(21902105);广东省特支计划人才项目;鹏城学者人才项目;深圳市科技计划(RCJC20200714114434086);深圳市科技计划(JCYJ20190808142001745);深圳市科技计划(JCYJ20200812160737002);深圳市科技计划(KQTD2016053112042971);广东省基础与应用基础研究基金(2020A1515010471);广东省普通高校青年创新人才项目(2018KQNCX221)

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

Wei Ou, Chuntian Qiu^*(), Chenliang Su^#()

SZU-NUS Collaborative Center and International Collaborative Laboratory of 2D Materials for Optoelectronic Science and Technology of Ministry of Education, College of Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, Guangdong, China

Received:2021-07-20 Accepted:2021-07-20 Online:2022-03-05 Published:2021-09-06
Contact: Chuntian Qiu, Chenliang Su
Supported by:
National Natural Science Foundation of China(21972094);fun: National Natural Science Foundation of China(21902105);Guangdong Special Support Program;Pengcheng Scholar Program;Shenzhen Science and Technology Program(RCJC20200714114434086);Shenzhen Science and Technology Program(JCYJ20190808142001745);Shenzhen Science and Technology Program(JCYJ20200812160737002);Shenzhen Science and Technology Program(KQTD2016053112042971);Guangdong Basic and Applied Basic Research Foundation(2020A1515010471);Foundation for Distinguished Young Talents in Higher Education of Guangdong(2018KQNCX221)

摘要/Abstract

摘要：

稳定氘同位素因其安全、易控制、廉价易得等优势而被广泛应用于探究有机反应机理和揭示药物及其代谢物的吸收、分布、代谢和排泄过程. 此外, 氘标记药物也被称为重氢药、重药, 即把药物分子上处于代谢位点的一个或多个碳氢键(C‒H)用碳氘键(C‒D)替代获得的新药, 以延长药物代谢周期、减少进入血液前的代谢、减少有毒代谢物产生, 从而降低给药剂量、提高安全性以及获得更佳的疗效. 2017年4月, 第一例氘代新药, 氘代四苯喹嗪(海外商品名Austedo, 国内商品名: 安泰坦)被美国食品药品监督管理局批准, 氘代新药市场被彻底激活. 临床数据显示, 丁苯那嗪原药具有严重的毒副作用, 19%的病人使用后表现出抑郁病症, 严重者甚至有自杀倾向; 氘代丁苯那嗪相对于原药, 代谢动力学特征明显改善, 毒副作用显著降低. 目前, 国内外已有多家知名药企(如BMS, Concert, Teva, 苏州泽璟生物制药以及成都海创等)布局氘代新药研发. 2021年6月, 中国国家药品监督管理局正式批准苯磺酸多纳非尼片(商品名: 泽普生), 用于治疗既往未接受过全身系统性治疗的不可切除肝细胞癌患者.
氘代药物的蓬勃发展使得对其精准合成提出了更高的要求和更强烈的需求. 氢氘交换等传统方法由于反应条件苛刻、氘源昂贵、氘代个数和位点难以精准控制等限制, 难以满足新时代氘代药物的发展需要. 近年, 化学家开始致力于开发温和、精准氘代新方法, 其中, 光或电驱动的温和、精准氘标记方法引起了广泛关注. 本综述着重总结近五年光/电驱动的温和、精准的氘代方法的研究进展. 基于氘原子引入的反应模式分为以下三种类型.
(1)氘原子转移策略: 以光/电催化单电子转移或者氢原子转移方式生成自由基中间体R^•; 随后, R^•与氘原子转移试剂(由硫醇和重水原位制得)反应, 得到相应的氘代产物R-D. 利用该策略, 目前已发展了羧酸、卤代烃、硫醚(醇)等的去官能化氘代反应以及硅烷、叔胺、醛基等的氢氘交换反应.
(2)氘原子攫取策略: 以光/电催化单电子转移、氢原子转移或者能量转移方式生成自由基R^•中间体, 一方面, 以产物碳氘键键能大于溶剂碳氘键键能为驱动力, 使R^•直接从氘代溶剂中攫取氘原子制得相应的氘代产物R-D; 另一方面, 利用光/电催化强驱动力, 使R^•再次获得一个电子形成相应负离子, 从而顺利从重水中攫氘, 制得相应的氘代产物R-D. 利用该策略, 目前已开发了羧酸、重氮、卤代物等的去官能化氘代反应, 以及亚胺的加氘还原反应.
(3)重水分解策略: 基于光/电催化水分解制氢原理, 以光或电为驱动力分解重水, 使其产生高活性氘物种, 原位耦合还原氘代反应. 利用该策略, 目前已开发了以重水为氘源的卤代物, 不饱和官能团(包括烯烃、炔烃、亚胺和芳基酮等)等的氘代还原反应以及伯、仲胺的氘甲基化反应.
本综述归纳了近年来光或电催化驱动的温和、精准氘代方法研究进展. 在此基础上结合课题组在该领域的研究经历, 分析了药物和精细化学品精准氘代面临的关键挑战和重要机遇, 包括: 发展温和、精准的不对称催化氘代方法用于制备手性氘代药物; 针对复杂药物多个代谢位点, 实现精准、可控氘代, 从而更有效调节药物代谢动力学和代谢产物. 此外, 光合成、电合成迅猛发展也将为氘代精细化学品和药物光、电催化合成带来新的机遇.

关键词: 光催化, 电催化, 氘代药物, 氢/氘原子转移, 单电子转移

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

欧伟, 邱春天, 苏陈良. 光、电催化合成氘代化学品和药物分子研究综述[J]. 催化学报, 2022, 43(4): 956-970.

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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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(21)63928-1

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

图/表 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.

参考文献

[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.

光、电催化合成氘代化学品和药物分子研究综述

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

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