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

Hydroboration reactions of carboxylic acids by sodium aminodiboranate (Na[BH₃NH₂BH₃], NaADBH) to form primary alcohols were systematically investigated and reduction mechanism was elucidated experimentally and computationally. Transfer of hydride ions from the B atom to the C atom, the key step in the mechanism, was theoretically illustrated and supported by experimental results. The intermediates of NH₂B₂H₅, PhCH=CHCOOBH₂NH₂BH₃^‒, PhCH=CHCH₂OBO, the by-products of BH₄^‒, NH₂BH₂, and NH₂BH₃^‒ were identified and characterized by ¹¹B and ¹H NMR or mass spectra. The reducing capacity of NaADBH was found between that of NaBH₄ and LiAlH₄. We have thus found that NaADBH is a promising reducing agent for the hydroboration due to its stability and easy-handling. These reactions have excellent yields and good selectivity, therefore providing alternative synthetic approaches for the conversion of carboxylic acids to primary alcohols with a wide range of functional group tolerance.

期刊年卷期页码：J. Org. Chem. 2021, 86, 5305−5316

链接地址：https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c00302