Palladium-catalysed cross-coupling of vinyldisiloxanes with benzylic and allylic halides and sulfonates.
The Hiyama cross-coupling reaction is a powerful method for carbon-carbon bond formation. To date, the substrate scope of this reaction has predominantly been limited to sp(2)-sp(2) 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.
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
Elizabeth C
EC
Frye
Cornelius J
CJ
O'Connor
David G
DG
Twigg
Bryony
B
Elbert
Luca
L
Laraia
David G
DG
Hulcoop
Ashok R
AR
Venkitaraman
David R
DR
Spring
D001190:Arylsulfonates / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D012833:Siloxanes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D001190:Arylsulfonates; D001555:Benzene Derivatives; D006846:Hydrocarbons, Halogenated; D012833:Siloxanes; D014753:Vinyl Compounds; D010165:Palladium