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Palladium‐Catalyzed Cascade Carbonylation to α,β‐Unsaturated Piperidones via Selective Cleavage of Carbon–Carbon Triple Bonds
Author(s) -
Ge Yao,
Ye Fei,
Yang Ji,
Spannenberg Anke,
Jiao Haijun,
Jackstell Ralf,
Beller Matthias
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202108120
Subject(s) - carbonylation , palladium , catalysis , chemistry , triple bond , bond cleavage , combinatorial chemistry , cascade reaction , cleavage (geology) , cascade , organic chemistry , carbon monoxide , double bond , materials science , chromatography , fracture (geology) , composite material
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.