Suzuki-Miyaura Cross-Coupling of Esters by Selective O-C(O) Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]₂ Precatalysts: Catalyst Evaluation and Mechanism.

ABSTRACT: The cross-coupling of aryl esters has emerged as a powerful platform for the functionalization of otherwise inert acyl C-O bonds in chemical synthesis and catalysis. Herein, we report a combined experimental and computational study on the acyl Suzuki-Miyaura cross-coupling of aryl esters mediated by well-defined, air- and moisture-stable Pd(II)-NHC precatalysts [Pd(NHC)(μ-Cl)Cl]₂. We present a comprehensive evaluation of [Pd(NHC)(μ-Cl)Cl]₂ precatalysts and compare them with the present state-of-the-art [(Pd(NHC)allyl] precatalysts bearing allyl-type throw-away ligands. Most importantly, the study reveals [Pd(NHC)(μ-Cl)Cl]₂ as the most reactive precatalysts discovered to date in this reactivity manifold. The unique synthetic utility of this unconventional O-

SUBMITTER: Yang S 

PROVIDER: S-EPMC8240519 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature