Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids.

ABSTRACT: 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(sp²)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.

SUBMITTER: Liu C 

PROVIDER: S-EPMC9069321 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature