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- Title
Reversible 1,1-Hydroboration: Boryl Insertion into a CN Bond and Competitive Elimination of HBR<sub>2</sub> or RH.
- Authors
Yang, Deng-Tao; Mellerup, Soren K.; Wang, Xiang; Wang, Suning; Lu, Jia-Sheng
- 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 CN 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 RH 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.
- Subjects
HYDROBORATION; HETEROCYCLIC compounds; BORANES; CHEMICAL reagents; X-ray diffraction
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 18, p5498
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201500487