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Palladium-Catalyzed Cascade Carbonylation to α,β-Unsaturated Piperidones via Selective Cleavage of Carbon-Carbon Triple Bonds.

ABSTRACT: A direct and selective synthesis of α,β-unsaturated piperidones by a new palladium-catalyzed cascade carbonylation is described. In the presented protocol, easily available propargylic alcohols react with aliphatic amines to provide a broad variety of interesting heterocycles. Key to the success of this transformation is a remarkable catalytic cleavage of the present carbon-carbon triple bond by using a specific catalyst with 2-diphenylphosphinopyridine as ligand and appropriate reaction conditions. Mechanistic studies and control experiments revealed branched unsaturated acid 11 as crucial intermediate.

SUBMITTER: Ge Y

PROVIDER: S-EPMC8519052 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Cascade Carbonylation to α,β-Unsaturated Piperidones via Selective Cleavage of Carbon-Carbon Triple Bonds.

Ge Yao Y Ye Fei F Yang Ji J Spannenberg Anke A Jiao Haijun H Jackstell Ralf R Beller Matthias M

Angewandte Chemie (International ed. in English) 20210906 41

A direct and selective synthesis of α,β-unsaturated piperidones by a new palladium-catalyzed cascade carbonylation is described. In the presented protocol, easily available propargylic alcohols react with aliphatic amines to provide a broad variety of interesting heterocycles. Key to the success of this transformation is a remarkable catalytic cleavage of the present carbon-carbon triple bond by using a specific catalyst with 2-diphenylphosphinopyridine as ligand and appropriate reaction conditi ...[more]

PMID: 34382728

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