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Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes.

ABSTRACT: A nickel-catalyzed regioselective addition/cyclization of o-(cyano)phenyl propargyl ethers with arylboronic acids has been developed, which provides an efficient protocol for the synthesis of highly functionalized 1-naphthylamines with wide structural diversity. The reaction is characterized by a regioselective and anti-addition of the arylboronic acids to the alkyne and subsequent facile nucleophilic addition of the resulting alkenylmetal to the tethered cyano group. Mechanistic studies reveal that a Ni(i) species might be involved in the catalytic process.

SUBMITTER: Zhang X

PROVIDER: S-EPMC6021782 | biostudies-other | 2016 Sep

REPOSITORIES: biostudies-other

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Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes.

Zhang Xingjie X Xie Xin X Liu Yuanhong Y

Chemical science 20160519 9

A nickel-catalyzed regioselective addition/cyclization of o-(cyano)phenyl propargyl ethers with arylboronic acids has been developed, which provides an efficient protocol for the synthesis of highly functionalized 1-naphthylamines with wide structural diversity. The reaction is characterized by a regioselective and anti-addition of the arylboronic acids to the alkyne and subsequent facile nucleophilic addition of the resulting alkenylmetal to the tethered cyano group. Mechanistic s ...[more]

PMID: 30034720

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