Nickel‐Catalyzed Alkoxy–Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers | Zendy

Guo Lin | Zendy; Liu Xiangqian | Zendy; Baumann Christoph | Zendy; Rueping Magnus | Zendy

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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.

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