Issue 26, 2008

Toward selective functionalisation of oligosilanes: borane-catalysed dehydrogenative coupling of silanes with thiols

Abstract

Among established methods for transforming Si–H bonds, carbonyl hydrosilylation and heterodehydrogenative coupling with alcohols catalysed by B(C6F5)3 are shown to provide exceptionally clean routes to the derivatisation of tetra-substituted disilanes such as [Ph2SiH]2, giving no products resulting from Si–Si bond cleavage. Even higher activity is observed for the borane-catalysed dehydrogenative coupling of silanes with alkyl- and arylthiols, the first examples of such Si–S bond formation in the absence of a transition metal catalyst. Clean, quantitative syntheses of a range of thiosilanes are reported, and the lability of the Si–S linkage toward subsequent alcoholysis is investigated. The crystal structure of 2,3-disila-2,2,3,3-tetramethyl-1,4-benzodioxane is presented.

Graphical abstract: Toward selective functionalisation of oligosilanes: borane-catalysed dehydrogenative coupling of silanes with thiols

Supplementary files

Article information

Article type
Paper
Submitted
14 Apr 2008
Accepted
12 May 2008
First published
02 Jun 2008

Dalton Trans., 2008, 3401-3411

Toward selective functionalisation of oligosilanes: borane-catalysed dehydrogenative coupling of silanes with thiols

D. J. Harrison, D. R. Edwards, R. McDonald and L. Rosenberg, Dalton Trans., 2008, 3401 DOI: 10.1039/B806270F

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