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Hydroboration Reaction and Mechanism of Carboxylic Acids using NaNH2(BH3)2, a Hydroboration Reagent with Reducing Capability between NaBH4 and LiAlH4

Jin Wang, Ming-Yue Ju, Xinghua Wang, Yan-Na Ma*, Donghui Wei* and Xuenian Chen*

*Henan Normal University, Xinxiang 453007; Zhengzhou University, Zhengzhou 450001, China, Email: mayannahtu.edu.cn, donghuiweizzu.edu.cn, xnchenhtu.edu.cn

J. Wang, M.-Y. Ju, X. Wang, Y.-N. Ma, D. Wei, X. Chen, J. Org. Chem., 2021, 86, 5305-5316.

DOI: 10.1021/acs.joc.1c00302 (free Supporting Information)


Abstract

Sodium aminodiboranate (NaNH2(BH3)2, NaADBH) is a promising reducing agent for hydroboration because of its stability and easy handling. Hydroboration reactions of carboxylic acids using NaADBH provide primary alcohols with excellent yields and good selectivity. This alternative synthetic approach tolerates a wide range of functional groups.

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proposed mechanism



Sodium Aminodiboranate, a New Reagent for Chemoselective Reduction of Aldehydes and Ketones to Alcohols

J. Wang, Y. Guo, S. Li, X. Chen, Synlett, 2021, 32, 1104-1108.


Key Words

reduction of carboxylic acids, NaADBH


ID: J42-Y2021