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A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes.

ABSTRACT: A chemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful ?-alkynyl-?, ?-unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density-functional theory (M06L-SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3-diynes.

SUBMITTER: Liu J

PROVIDER: S-EPMC7821284 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes.

Liu Jiawang J Schneider Carolin C Yang Ji J Wei Zhihong Z Jiao Haijun H Franke Robert R Jackstell Ralf R Beller Matthias M

Angewandte Chemie (International ed. in English) 20201027 1

A chemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α-alkynyl-α, β-unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density-functional theory (M06L- ...[more]

PMID: 32959449

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