Arene C-H borylation strategy enabled by a non-classical boron cluster-based electrophile.

ABSTRACT: Introducing a tri-coordinate boron-based functional group (e.g., boronic ester) into an unactivated C-H bond in the absence of directing groups is an ongoing challenge in synthetic chemistry. Despite previous developments in transition metal-catalyzed and -free approaches, C-H borylation of sterically hindered arenes remains a largely unsolved problem to date. Here, we report a synthetic strategy of a two-step, precious metal-free electrophilic C-H borylation of sterically hindered alkyl- and haloarenes to generate aryl boronic esters. The first step relies on electrophilic aromatic substitution (EAS) induced by cage-opening of Cs₂[closo-B₁₀H₁₀], forming a 6-Ar-nido-B₁₀H₁₃ product containing a B-C bond, followed by a cage deconstructio

SUBMITTER: Kim S 

PROVIDER: S-EPMC10039867 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature