Gold Is Not Palladium: Linear Selectivity in Gold-Catalyzed Heck-Type Arylation via an Allylic Deprotonation-Coupling (ADC) Mechanism.

ABSTRACT: Gold-catalyzed arylation of alkenes has recently been reported by Patil and co-workers as a rare example of a Heck-type reaction exhibiting exclusive linear selectivity. However, no mechanistic rationale was provided for the complete suppression of the branched product. In this study, we address this gap through DFT calculations and show that if the reaction proceeds via the classical Heck-type pathway, formation of the branched product is energetically preferred, which is inconsistent with experimental observations. This discrepancy led us to identify a distinct mechanistic alternative: an allylic deprotonation-coupling (ADC) mechanism, in which alkene-gold(III) complexes undergo early allylic C-H deprotonation followed by C-C reductive elimination. The ADC mechanism is found to be energe

SUBMITTER: Farshadfar K 

PROVIDER: S-EPMC12606697 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature