TY - JOUR
T1 - Palladium-Catalysed Cross-Coupling of Vinyldisiloxanes with Benzylic and Allylic Halides and Sulfonates
AU - Frye, Elizabeth C.
AU - O'Connor, Cornelius J.
AU - Twigg, David G.
AU - Elbert, Bryony
AU - Laraia, Luca
AU - Hulcoop, David G.
AU - Venkitaraman, Ashok R.
AU - Spring, David R.
PY - 2012
Y1 - 2012
N2 - 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.
AB - 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.
U2 - 10.1002/chem.201200431
DO - 10.1002/chem.201200431
M3 - Journal article
VL - 18
SP - 8774
EP - 8779
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 28
ER -
