Comparative DFT study of metal-free Lewis acid-catalyzed C-H and N-H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope.

ABSTRACT: Direct selective dehydrogenative silylation of thiophenes, pyridines, indoles and anilines to synthesize silyl-substituted aromatic compounds catalyzed by metal-free Lewis acids was achieved recently. However, there is still insufficient mechanistic data for these transformations. Using density functional theory calculations, we conducted a detailed investigation of the mechanism of the B(C₆F₅)₃-catalyzed dehydrogenative silylation of N-methylindole, N,N-dimethylaniline and N-methylaniline. We successfully located the most favourable reaction pathways that can explain the experimental observations notably well. The most favourable pathway for B(C₆F₅)₃-catalyzed C-H silylation of N-methylind

SUBMITTER: Du P 

PROVIDER: S-EPMC9075773 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature