Palladium(I)-Iodide-Catalyzed Deoxygenative Heck Reaction of Vinyl Triflates: A Formate-Mediated Cross-Electrophile Reductive Coupling with <i>cine</i>-Substitution.

ABSTRACT: The first deoxygenative Heck reactions are described, as illustrated by formate-mediated cine-substitutions of vinyl triflates with aryl iodides. The collective data corroborate a mechanism in which Pd(OAc)₂ and Bu₄NI form the dianionic iodide-bridged dimer [Pd₂I₆][NBu₄]₂, which, under reducing conditions, serves as a precursor to the palladium(I) complex [Pd₂I₄][NBu₄]₂. Dinculear oxidative addition of aryl iodide forms [Pd₂I₅(Ar)][NBu₄]₂, which dissociates to the monometallic complex [PdI₂(Ar)][NBu₄]. Vinyl triflate migratory insertion-sulfonate elimination delivers a palladium(IV) carbene, which upon β-hydri

SUBMITTER: Chang YH 

PROVIDER: S-EPMC10615887 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature