Preparation of Allyl and Vinyl Silanes via the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction

Preparation of Allyl and Vinyl Silanes via the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction

A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes using silyl halides is reported. This method allows facile conversion of styrenes to E -β-silyl styrenes using either TMSI or TMSCl/LiI. Terminal allyl silanes with good E:Z ratios are also readily accessed from α-ol...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-03, Vol.51 (15), p.3663-3667
Hauptverfasser: McAtee, Jesse R., Martin, Sara E. S., Ahneman, Derek T., Johnson, Keywan A., Watson, Donald A.
Format: Artikel
Sprache:eng
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Zusammenfassung:A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes using silyl halides is reported. This method allows facile conversion of styrenes to E -β-silyl styrenes using either TMSI or TMSCl/LiI. Terminal allyl silanes with good E:Z ratios are also readily accessed from α-olefins by this method. When combined with existing technology, this transformation provides a powerful strategy to selectively functionalize the vinyl or allylic position of terminal alkenes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201200060