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n-Butyllithium Catalyzed Selective Hydroboration of Aldehydes and Ketones

Author:
Zhu, Zhangye, Wu, Xueli, Xu, Xiaojuan, Wu, Zhenjie, Xue, Mingqiang, Yao, Yingming, Shen, Qi, Bao, Xiaoguang
Source:
Journal of organic chemistry 2018 v.83 no.17 pp. 10677-10683
ISSN:
1520-6904
Subject:
aldehydes, catalysts, catalytic activity, chemical reactions, ketones, moieties, organic chemistry
Abstract:
Highly efficient and selective hydroboration of aldehydes and ketones with HBpin is achieved by using the simple and convenient n-BuLi as a catalyst. The reaction proceeds rapidly with low catalyst loading (0.1–0.5 mol %) under mild conditions. Key features include the high catalytic efficiency, exceptional functional group compatibility, ample substrate scope, and high selectivity for aldehydes over ketones. Computational studies were carried out to provide a mechanistic insight into the n-BuLi catalyzed hydroboration of aldehydes/ketones with HBpin.
Agid:
6127114