Reversible 1,1‐Hydroboration: Boryl Insertion into a CN Bond and Competitive Elimination of HBR2 or RH |
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| Authors: | Deng‐Tao Yang Soren K. Mellerup Xiang Wang Dr. Jia‐Sheng Lu Prof. Dr. Suning Wang |
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| Affiliation: | 1. Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6 (Canada);2. Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing (P.R. China) |
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| 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 . |
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| Keywords: | 1,1‐hydroboration BN heterocycles boryl insertion thermal elimination |
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