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

Abstract

Sodium aminodiboranate (NaNH₂(BH₃)₂, NaADBH) is a new member of the old borane family, which exhibits superior performance in chemoselective reduction. Experimental results show that NaADBH can rapidly reduce aldehydes and ketones to the corresponding alcohols in high efficiency and selectivity under mild conditions. There are little steric and electronic effects on this reduction.

Key words

sodium aminodiboranate - hydrogenation - reduction - aldehydes - ketones

Publication History

Received: 17 March 2021

Accepted after revision: 10 April 2021

Accepted Manuscript online:
10 April 2021

Article published online:
06 May 2021

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• 16 Typical Experimental Procedure A solution of NaADBH (1 mmol, 1.0 equiv) in THF (5 mL) was added into the solution of benzaldehyde (3.0 mmol, 3.0 equiv) in THF (5 mL) at room temperature under air atmosphere. The progress of the reaction was monitored by TLC. Upon completion, the hydrolysis of borate esters was carried out by addition of excess water, forming the corresponding alcohols and trimethylborate. The reaction mixture was extracted with EtOAc (3 × 20 mL) and CH₂Cl₂ (3 × 20 mL). The combined organic extracts were dried over anhydrous Na₂SO₄ and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography to obtain the product 1a as a colorless liquid (301 mg, 2.79 mmol, 93%). ¹H NMR (600 MHz, CDCl₃): δ = 7.26–7.20 (m, 2 H), 7.20–7.14 (m, 3 H), 4.40 (s, 2 H), 4.04 (s, 1 H). ¹³C NMR (151 MHz, CDCl₃): δ = 140.9, 128.6, 127.7, 127.1, 65.3.
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