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Electrocatalytic Deuteration of Halides with D 2 O as the Deuterium Source over a Copper Nanowire Arrays Cathode
Author(s) -
Liu Cuibo,
Han Shuyan,
Li Mengyang,
Chong Xiaodan,
Zhang Bin
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202009155
Subject(s) - deuterium , halide , cathode , copper , reagent , bromide , chemoselectivity , anode , chemistry , halogenation , inorganic chemistry , electrode , catalysis , organic chemistry , physics , quantum mechanics
Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D 2 O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross‐coupling of carbon and deuterium free radicals might be involved for this ipso‐selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C−H to C−D transformations were achieved with high yields and deuterium ratios through a one‐pot halogenation–deuterodehalogenation process. Efficient deuteration of less‐active bromide substrates, specific deuterium incorporation into top‐selling pharmaceuticals, and oxidant‐free paired anodic synthesis of high‐value chemicals with low energy input highlighted the potential practicality.