Pd(0)-Catalyzed Intermolecular Methylene C(sp3)-H Silylation by Using N-Heterocyclic Carbene Ligands

Zhengyang Zhang; Feng Wei; Xuan Wang; Yanghui Zhang

doi:10.1021/acs.orglett.4c01044

Pd(0)-Catalyzed Intermolecular Methylene C(sp³)-H Silylation by Using N-Heterocyclic Carbene Ligands

Org Lett. 2024 May 3;26(17):3586-3590. doi: 10.1021/acs.orglett.4c01044. Epub 2024 Apr 23.

Authors

Zhengyang Zhang¹, Feng Wei¹, Xuan Wang², Yanghui Zhang¹

Affiliations

¹ School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, Shanghai 200092, China.
² Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, China.

PMID: 38651729
DOI: 10.1021/acs.orglett.4c01044

Abstract

The direct functionalization of methylene C(sp³)-H bonds is one of the greatest challenges in transition metal-catalyzed C-H activation. Although Pd(0)-catalyzed intramolecular cyclization reactions of methylene C(sp³)-H bonds have been reported, intermolecular functionalization remains to be discovered. Herein, we report the first example of a Pd(0)-catalyzed intermolecular methylene C(sp³)-H functionalization reaction. By use of a N-heterocyclic carbene ligand, the methylene C(sp³)-H bonds of 1-(benzyloxy)-2-iodobenzenes are activated and disilylated with hexamethyldisilane, affording disilylated products.