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Cobalt‐Catalyzed Dehydrogenative Coupling of Alcohols/Aldehydes and Amines: An Important Role for Imine Hydration
Author(s) -
Guo YaFei,
Ren TianLu,
Xu BaoHua,
Wang YaoFeng,
Zhang SuoJiang
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500514
Subject(s) - chemistry , hemiaminal , catalysis , cobalt , imine , hydrogen atom abstraction , iodide , amine gas treating , radical , organic chemistry , combinatorial chemistry , medicinal chemistry , photochemistry
A cobalt and iodide co‐catalyzed oxidative amidation reaction between alcohols or aldehydes and amines has been developed. The reactions proceeded smoothly under mild conditions using tert ‐butyl hydroperoxide solution in water as the terminal oxidant, with broad functional group tolerance. Mechanistic studies indicated that the t BuO ⋅ / t BuOO ⋅ radical generated in situ is the active species responsible for hydrogen abstraction in this catalytic process, and not IO − /IO 2 − /IO 3 − ions. Investigation into the reaction mechanism also revealed the potential transiency of a hemiaminal and the important role of its regeneration by imine hydration.