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Synlett 2007(4): 0666-0667  
DOI: 10.1055/s-2007-967957
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Catecholborane, a Convenient Boron Reagent

Bangle Zhang*
Institute of Materia Medica, Shanghai Institutes for Biological ­Sciences, Chinese Academy of Sciences, Shanghai, P. R. of China
e-Mail: blezhang@hotmail.com;
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Publication History

Publication Date:
21 February 2007 (online)

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Introduction

Catecholborane (1), known as 1,3,2-benzodioxaborole, is a versatile boron hydride reagent commercially available for synthetic organic chemistry. It is stable towards dry air and easily soluble in organic solvents. Apart from its well-known application as a new hydroborating agent in some transformations, [1] it has found a multitude of applications in reduction of various organic functional groups, organo­borane-mediated cyclizations, carboxyl activation of ­carboxylic acids and deprotection of some functional groups. When catecholborane was associated with chiral oxazaborolidine and chiral transition-metal-complex ­catalysts, a novel way to synthesize chiral alcohols in very high enantioselectivities was presented. Catecholborane can be conveniently prepared by several approaches, [2] and the preferred synthesis was the reaction of catechol with borane-tetrahydrofuran or borane-methyl sulfide. [3]