Open AccessDecarbonylative Sonogashira Cross-Coupling of Carboxylic Acids
Author(s) -
Chengwei Liu,
Michal Szostak
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01445
Subject(s) - chemistry , transmetalation , decarbonylation , sonogashira coupling , xantphos , carboxylic acid , aryl , palladium , derivatization , carbodiimide , combinatorial chemistry , electrophile , organic chemistry , catalysis , alkyl , high performance liquid chromatography
Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc) 2 /Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp 2 )-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.