A Zinc Catalyzed C(sp³ )-C(sp² ) Suzuki-Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates.

ABSTRACT: The Suzuki-Miyaura (SM) reaction is one of the most important methods for C-C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr₂ , in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.

SUBMITTER: Procter RJ 

PROVIDER: S-EPMC5915750 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature