Simple and convenient n-BuLi is reported as a highly efficient catalyst in promoting the hydroboration of imines and alkynes.

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.

Herein, we present a facile method for deoxygenative hydroboration of a broad range of carboxylic acids under very mild conditions. The most striking feature of this attractive hydroboration is that this elusive and challenging transformation was realized without catalyst and solvent. The investigation of solvent effect showed that tetrahydrofuran was also suitable for this kind of reaction. Moreover, a successful gram-scale trial may provide a very promising toolkit for carboxylic acid reduction at a large scale.

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