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Palladium‐Catalyzed Intermolecular Acylation of Aryl Diazoesters with ortho ‐Bromobenzaldehydes
Author(s) -
Yu Yinghua,
Lu Qianqian,
Chen Gui,
Li Chunsen,
Huang Xueliang
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.201710317
Subject(s) - chemistry , palladium , isocoumarin , migratory insertion , aryl , acylation , catalysis , reductive elimination , medicinal chemistry , carbene , intermolecular force , aldehyde , stereochemistry , combinatorial chemistry , organic chemistry , molecule , alkyl
In this work, we describe a palladium‐catalyzed intermolecular O acylation of α‐diazoesters with ortho ‐bromobenzaldehydes. The C(sp 2 )−H bond activation of the aldehyde is enabled by migratory insertion of a palladium carbene intermediate. The diazoesters act as modular three‐atom units to build up key seven‐membered palladacycles, which are transformed into a variety of isocoumarin derivatives upon reductive elimination. Mechanistic experiments and DFT calculations provide insight into the reaction pathway.