NHC-catalyzed dehydrogenative self-coupling of diphenylsilane: a facile synthesis of octaphenylcyclotetra(siloxane)

by Albright, Abigail Lynn; Gawley, Robert E.

A unique application of the CulPr N-heterocyclic carbene (NHC) to the dehydrogenative self-coupling of diphenylsilane has been discovered. This transformation is carried out open to air at room temperature, yielding octaphenylcyclotetra(siloxane) quantitatively in 1 h. This preparation constitutes a significant improvement over existing methods for the preparation of this compound and demonstrates a novel mode of reactivity for CuIPr. The diphenylsilanone tetramer is the precursor to a number of industrially significant polymers. (C) 2011 Elsevier Ltd. All rights reserved.

Journal
Tetrahedron Letters
Volume
52
Issue
46
Year
2011
Start Page
6130
URL
http://www.sciencedirect.com/science/article/pii/S0040403911015498
ISBN/ISSN
1873-3581; 0040-4039
PMID
22058577
DOI
10.1016/j.tetlet.2011.09.028