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A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes
Author(s) -
Liu Jiawang,
Schneider Carolin,
Yang Ji,
Wei Zhihong,
Jiao Haijun,
Franke Robert,
Jackstell Ralf,
Beller Matthias
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010768
Subject(s) - regioselectivity , palladium , catalysis , stereoselectivity , combinatorial chemistry , ligand (biochemistry) , chemistry , substrate (aquarium) , stereochemistry , organic chemistry , biology , receptor , ecology , biochemistry
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‐SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3‐diynes.