Desulfurative Deuteration of (Hetero)Aryl Sulfides With D <sub>2</sub> O by Nickel Catalysis
Abstract
ABSTRACT Selective deuteration of (hetero)aryl rings is of great significance and interest, yet it has remained a challenge, especially when employing D 2 O as deuterium source. Herein, the selective desulfurative deuteration of widely available (hetero)aryl sulfides with D 2 O (mostly 1.5 or 3.0 equiv.) has been established by nickel catalysis. This strategy affords an efficient and robust route for the synthesis of a wide range of deuterated (hetero)arenes (87 examples, > 10 different heterocycles) in generally good yields and high deuterium incorporation with good functional group compatibility. The catalytic reaction could be applied to scaled‐up synthesis (e.g., 6.4 g for product 2 , 0.1 mol% Ni catalyst, 590 TON) and late‐stage deuteration of various drugs and bioactive molecules.
Article Details
Authors (9)
Yaqi Chen
Qian Ni
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), Key Laboratory of Phytochemical R&D of Hunan Province, and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Institute of Interdisciplinary Studies, College of Chemistry and Chemical Engineering Hunan Normal University Changsha People's Republic of China
Long Tian
Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry
Weiqi Song
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), Key Laboratory of Phytochemical R&D of Hunan Province, and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Institute of Interdisciplinary Studies, College of Chemistry and Chemical Engineering Hunan Normal University Changsha People's Republic of China
Mingyang Long
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), Key Laboratory of Phytochemical R&D of Hunan Province, and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Institute of Interdisciplinary Studies, College of Chemistry and Chemical Engineering Hunan Normal University Changsha People's Republic of China
Ming Ma
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Haidian District, Beijing 100191, China
Han Zuilhof
Bo Chen
Yuanhong Ma