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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

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Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids.

Liu Chengwei C Szostak Michal M

Organic letters 20210607 12

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)<sub>2</sub>/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(s ...[more]

PMID: 34096312

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