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Palladium‐Catalyzed Alkene Thioacylation: A C−S Bond Activation Approach for Accessing Indanone Derivatives
Author(s) -
Wu Jianing,
Xu WenHua,
Lu Hong,
Xu PengFei
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100293
Subject(s) - chemistry , decarbonylation , alkene , palladium , substituent , intramolecular force , thioester , catalysis , organopalladium , migratory insertion , alkyl , reductive elimination , medicinal chemistry , insertion reaction , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , enzyme
A palladium‐catalyzed intramolecular alkene thioacylation reaction initiated by the activation of thioester C(acyl)−S bonds is reported. This approach successfully suppressed decarbonylation and β‐hydrogen elimination with related acyl and alkyl metal thiolate intermediates, providing an efficient and atom‐economical method to access indanone scaffolds. Mechanistic studies provide support for C(acyl)−Pd bond insertion of olefins. The synthetic utility of this protocol is demonstrated by the further conversion of the newly formed methylene sulfide substituent.