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Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3‐Diynes
Author(s) -
Liu Jiawang,
Yang Ji,
Schneider Carolin,
Franke Robert,
Jackstell Ralf,
Beller Matthias
Publication year - 2020
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.201915386
Subject(s) - palladium , conjugated system , carbonylation , aryl , catalysis , combinatorial chemistry , chemistry , ligand (biochemistry) , bicyclic molecule , organic chemistry , receptor , carbon monoxide , biochemistry , alkyl , polymer
For the first time, the monoalkoxycarbonylation of easily available 1,3‐diynes to give synthetically useful conjugated enynes has been realized. Key to success was the design and utilization of the new ligand 2,2′‐bis( tert ‐butyl(pyridin‐2‐yl)phosphanyl)‐1,1′‐binaphthalene (Neolephos), which permits the palladium‐catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3‐enynes in good‐to‐high yields with excellent chemoselectivities. Synthetic applications that showcase the possibilities of this novel methodology include an efficient one‐pot synthesis of 4‐aryl‐4 H ‐pyrans as well as the rapid construction of various heterocyclic, bicyclic, and polycyclic compounds.