Palladium-Catalysed Cross-Coupling of Vinyldisiloxanes with Benzylic and Allylic Halides and Sulfonates

Elizabeth C. Frye, Cornelius J. O'Connor, David G. Twigg, Bryony Elbert, Luca Laraia, David G. Hulcoop, Ashok R. Venkitaraman, David R. Spring

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The Hiyama cross-coupling reaction is a powerful method for carboncarbon bond formation. To date, the substrate scope of this reaction has predominantly been limited to sp2-sp2 coupling reactions. Herein, the palladium-catalysed Hiyama type cross-coupling of vinyldisiloxanes with benzylic and allylic bromides, chlorides, tosylates and mesylates is reported. A wide variety of functional groups were tolerated, and the synthetic utility of the methodology was exemplified through the efficient total synthesis of the cytotoxic natural product bussealin A. In addition, the antiproliferative ability of bussealin A was evaluated in two cancer-cell lines.
Original languageEnglish
JournalChemistry-a European Journal
Volume18
Issue number28
Pages (from-to)8774-8779
ISSN0947-6539
DOIs
Publication statusPublished - 2012
Externally publishedYes

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