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Palladium‐Catalyzed Oxygenative Cross‐Coupling of Ynamides and Benzyl Bromides by Carbene Migratory Insertion
Author(s) -
Gao Yunpeng,
Wu Guojiao,
Zhou Qi,
Wang Jianbo
Publication year - 2018
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.201712795
Subject(s) - carbene , palladium , migratory insertion , chemistry , catalysis , intermolecular force , amide , coupling reaction , coupling (piping) , medicinal chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , materials science , metallurgy
Abstract A palladium‐catalyzed oxygenative cross‐coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α‐disubstituted amide derivatives were obtained in good yields. Migratory insertion of α‐oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step in this reaction. The study demonstrates the potential of ynamides to serve as carbene precursors in palladium‐catalyzed C−C bond‐forming cross‐coupling reactions.