Journal
TETRAHEDRON
Volume 64, Issue 22, Pages 5322-5327Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.03.024
Keywords
cross-couplings; organosilanes; Pd-catalyzed reactions; tris(trimethylsilyl)silanes
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Funding
- NIGMS NIH HHS [R25 GM061347, S06 GM008205-220028, S06 GM008205] Funding Source: Medline
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The oxidative treatment of vinyl tris(trimethyl silyl)si lanes with hydrogen peroxide in aqueous sodium hydroxide in tetrahydrofuran generates reactive silanol or siloxane species that undergo Pd-catalyzed cross-couplings with aryl, heterocyclic, and alkenyl halides in the presence of Pd(PPh3)(4) and tetrabutylammonium fluoride. Hydrogen peroxide and base are necessary for the coupling to occur while activation of the silanes with fluoride is not required. The conjugated and unconjugated tris(trimethylsilyl)silanes serve as good cross-coupling substrates. The (E)-silanes undergo coupling with retention of stereochemistry while coupling of (Z)-silanes occurred with lower stereoselectivity to produce an E/Z mixture of products. (C) 2008 Elsevier Ltd. All rights reserved.
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