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Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles.

ABSTRACT: Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved.

SUBMITTER: Ye C

PROVIDER: S-EPMC6432612 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles.

Ye Changqing C Li Yajun Y Zhu Xiaotao X Hu Shengmin S Yuan Daqiang D Bao Hongli H

Chemical science 20190219 12

Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved. ...[more]

PMID: 30996957

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