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Chemoselective, Scalable Nickel‐Electrocatalytic O ‐Arylation of Alcohols
Author(s) -
Zhang HaiJun,
Chen Longrui,
Oderinde Martins S.,
Edwards Jacob T.,
Kawamata Yu,
Baran Phil S.
Publication year - 2021
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.202107820
Subject(s) - aryl , chemistry , combinatorial chemistry , nucleophile , catalysis , nickel , substrate (aquarium) , halide , chemoselectivity , alkyl , ether , electrochemistry , amine gas treating , transition metal , organic chemistry , oceanography , electrode , geology
The formation of aryl‐alkyl ether bonds through cross coupling of alcohols with aryl halides represents a useful strategic departure from classical S N 2 methods. Numerous tactics relying on Pd‐, Cu‐, and Ni‐based catalytic systems have emerged over the past several years. Herein we disclose a Ni‐catalyzed electrochemically driven protocol to achieve this useful transformation with a broad substrate scope in an operationally simple way. This electrochemical method does not require strong base, exogenous expensive transition metal catalysts (e.g., Ir, Ru), and can easily be scaled up in either a batch or flow setting. Interestingly, e‐etherification exhibits an enhanced substrate scope over the mechanistically related photochemical variant as it tolerates tertiary amine functional groups in the alcohol nucleophile.