Mechanism and Selectivity of Copper-Catalyzed Bromination of Distal C(sp³)-H Bonds.

ABSTRACT: Unactivated C(sp³)-H bonds are the most challenging substrate class for transition metal-catalyzed C-H halogenation. Recently, the Yu group [Liu, T.; Myers, M. C.; Yu, J. Q. Angew. Chem., Int. Ed.2017, 56 (1), 306-309] has demonstrated that a Cu^II/phenanthroline catalyst and BrN₃, generated in situ from NBS and TMSN₃ precursors, can achieve selective C-H bromination distal to a directing group. The current understanding of the mechanism of this reaction has left numerous questions unanswered. Here, we investigated the mechanism of Cu-catalyzed C(sp³)-H bromination with distal site selectivity using density functional theory calculations. We found that this reaction starts with the Br-atom transfer from BrN

SUBMITTER: Ajitha MJ 

PROVIDER: S-EPMC10526628 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature