Issue 45, 2021

Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- and phosphine-boranes

Abstract

A highly versatile synthesis of amine-boranes via carbonyl reduction by sodium borohydride is described. Unlike the prior bicarbonate-mediated protocol, which proceeds via a salt metathesis reaction, the carbon dioxide-mediated synthesis proceeds via reduction to a monoformatoborohydride intermediate. This has been verified by spectroscopic analysis, and by using aldehydes and ketones as the carbonyl source for the activation of sodium borohydride. This process has been used to produce borane complexes with 1°-, 2°-, and 3°-amines, including those with borane reactive functionalities, heteroarylamines, and a series of phosphines.

Graphical abstract: Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- and phosphine-boranes

Supplementary files

Article information

Article type
Paper
Submitted
15 Oct 2021
Accepted
04 Nov 2021
First published
05 Nov 2021

Dalton Trans., 2021,50, 16770-16774

Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- and phosphine-boranes

P. Veeraraghavan Ramachandran, H. J. Hamann and R. Lin, Dalton Trans., 2021, 50, 16770 DOI: 10.1039/D1DT03495B

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