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n-Butyllithium catalyzed hydroboration of imines and alkynes

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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

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Publication details

The article was received on 28 Nov 2018, accepted on 14 Jan 2019 and first published on 15 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01289J
Citation: Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C8QO01289J

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