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Carbene Bridging C–H Activation: Facile Isocoumarin Synthesis Through Palladium‐Catalyzed Reaction of 2‐Pseudohalobenzaldehydes with Aryl Diazoesters
Author(s) -
Yan Chao,
Yu Yinghua,
Peng Bo,
Huang Xueliang
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901738
Subject(s) - carbene , chemistry , moiety , aryl , isocoumarin , palladium , migratory insertion , combinatorial chemistry , aldehyde , synthon , catalysis , stereochemistry , organic chemistry , alkyl
A reaction mode on carbene bridging C–H activation (CBA) is described. In this reaction, metal carbene was produced prior to the event of C–H bond metallation. Readily available aryl dizaoesters were employed as the carbene precursors. Migratory insertion of the palladium carbene intermediate could create a modular bridging arm to promote the C–H bond palladation of tethered aldehyde moiety. Its synthetic potential was demonstrated by facile construction isocoumarin scaffold from easily accessible starting materials. Furthermore, this protocol is also amenable for late‐functionalization of complex molecules.