Understanding and Expanding Zinc Cation/Amine Frustrated Lewis Pair Catalyzed C-H Borylation.

ABSTRACT: [(NacNac)Zn(DMT)][B(C₆F₅)₄], 1, (NacNac = {(2,6- ⁱ Pr₂H₃C₆)N(CH₃)C}₂CH), DMT = N,N-dimethyl-4-toluidine), was synthesized via two routes starting from either (NacNac)ZnEt or (NacNac)ZnH. Complex 1 is an effective (pre)catalyst for the C-H borylation of (hetero)arenes using catecholborane (CatBH) with H₂ the only byproduct. The scope included weakly activated substrates such as 2-bromothiophene and benzothiophene. Computational studies elucidated a plausible reaction mechanism that has an overall free energy span of 22.4 kcal/mol (for N-methylindole borylation), consistent with experimental observations. The calculated mechanism starting from 1<

SUBMITTER: Grundy ME 

PROVIDER: S-EPMC9942201 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature