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Nickel‐Catalyzed Alkoxy–Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers
Author(s) -
Guo Lin,
Liu Xiangqian,
Baumann Christoph,
Rueping Magnus
Publication year - 2016
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.201607646
Subject(s) - chemistry , alkylation , reagent , enol , aryl , chemoselectivity , catalysis , alkyl , alkoxy group , bond cleavage , nickel , medicinal chemistry , cleavage (geology) , catalytic cycle , combinatorial chemistry , organic chemistry , materials science , fracture (geology) , composite material
A nickel‐catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B ‐alkyl 9‐BBN and trialkylborane reagents that involves the cleavage of stable C(sp 2 )−OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp 2 )−C(sp 3 ) bonds that does not suffer from β‐hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C−O bonds is presented to demonstrate the advantage of this method.