Reversible 1, 1‐Hydroboration: Boryl Insertion into a CN Bond and Competitive Elimination of HBR2 or RH 1. Issue 18 (20th March 2015)

• Record Type: Journal Article
• Authors: Yang, Deng‐Tao; Mellerup, Soren K.; Wang, Xiang; Lu, Jia‐Sheng; Wang, Suning
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 18(2015)
• Page Start: 5498
• Page End: 5501
• Publication Date: 2015-03-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201500487
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Boranes with the general formula of HBR₂ have been found to undergo a facile 1, 1‐hydroboration reaction with pyrido[1, 2‐a]isoindole (<bold>A</bold>), 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 <bold>A</bold> was found to be the key intermediate in 1, 1‐hydroboration of <bold>A</bold>.</p> </abstract>