Intramolecular hydrosilylation and silicon-assisted cross-coupling: an efficient route to trisubstituted homoallylic alcohols.
[figure: see text] Alkylidenesilacyclopentanes (formed by intramolecular hydrosilylation of homopropargyl alcohols) are efficiently coupled with aryl or alkenyl halides in the presence of tetrabutylammonium fluoride and a palladium(0) catalyst. Yields of cross-coupling were generally high, and the reaction is compatible with a wide range of functional groups. The overall transformation achieves the conversion of homopropargyl alcohols to trisubstituted homoallylic alcohols in a highly stereoselective fashion.
Denmark
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245 Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
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