Issue 5, 2019

n-Butyllithium catalyzed hydroboration of imines and alkynes

Abstract

The first examples of the hydroboration of imines with HBpin catalyzed by the commercially available n-BuLi are reported herein. Good functional group tolerance under mild conditions and short reaction time have been achieved. Further investigation showed that n-BuLi could also serve as an efficient catalyst for the hydroboration of alkynes with HBpin. High chemoselectivity toward imines over alkynes is presented. A possible mechanistic pathway of the n-BuLi catalyzed hydroboration of imines with HBpin is proposed based on computational studies.

Graphical abstract: n-Butyllithium catalyzed hydroboration of imines and alkynes

Supplementary files

Article information

Article type
Research Article
Submitted
28 Nov 2018
Accepted
14 Jan 2019
First published
15 Jan 2019

Org. Chem. Front., 2019,6, 648-653

n-Butyllithium catalyzed hydroboration of imines and alkynes

D. Yan, X. Wu, J. Xiao, Z. Zhu, X. Xu, X. Bao, Y. Yao, Q. Shen and M. Xue, Org. Chem. Front., 2019, 6, 648 DOI: 10.1039/C8QO01289J

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