Site‐Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**
- 18 September 2021
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 60 (50), 26238-26245
- https://doi.org/10.1002/anie.202111978
Abstract
An unprecedented and general hydroboration of alkenes with BX3(X = Br, Cl) as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene polymerization and haloboration side reactions but also provides an "H" source for hydroboration. More importantly, the site-fixed installation of a boryl group at the original position of the internal double-bond is readily achieved as compared with conventional transition-metal-catalyzed hydroboration processes. Further application to the synthesis of 1, n-diborylalkanes (n=3-10) is also demonstrated. Preliminary mechanistic studies reveal a major reaction pathway that involves radical species and operates through frustrated-Lewis-pair-type single-electron transfer mechanism.Keywords
Funding Information
- National Natural Science Foundation of China (91845108, 21901247, 21902167, 22101114)
- Natural Science Foundation of Jiangsu Province (BK20180246)
- Southern University of Science and Technology (Y01216248)
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