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Beller, Matthias
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Ge, Yao
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cascade carbonylation
homogeneous catalysis
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bond cleavage
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palladium
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α,β-unsaturated piperidones
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Palladium-Catalyzed Cascade Carbonylation to α,β-Unsaturated Piperidones via Selective Cleavage of Carbon-Carbon Triple Bonds
(
Weinheim : Wiley-VCH,
2021
)
Ge, Yao
;
Ye, Fei
;
Yang, Ji
;
Spannenberg, Anke
;
Jiao, Haijun
;
Jackstell, Ralf
;
Beller, Matthias
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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. © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
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