title: Reversible 1,1-hydroboration: boryl insertion into a C-N bond and competitive elimination of HBR2 or R-H.
abstract: Boranes with the general formula of HBR2 have been found to undergo a facile 1,1-hydroboration reaction with pyrido[1,2-a]isoindole (A), resulting in insertion of a BR2 unit into a CN bond and the formation of a variety of BN heterocycles. Investigation on the thermal reactivity of the BN heterocycles revealed that these molecules have two distinct and competitive thermal elimination pathways: HBR2 elimination (or retro-hydroboration) versus RH elimination, depending on the R group on the B atom and the chelate backbone. Mechanistic aspects of these highly unusual reactions have been established from both experimental and computational evidence. Adduct formation between HBR2 and A was found to be the key intermediate in 1,1-hydroboration of A.
authors: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6 (Canada).
authors: Deng-Tao
authors: DT
authors: Yang
authors: Soren K
authors: SK
authors: Mellerup
authors: Xiang
authors: X
authors: Wang
authors: Jia-Sheng
authors: JS
authors: Lu
authors: Suning
authors: S
authors: Wang
keywords: 1,1-hydroboration; BN heterocycles; boryl insertion; thermal elimination