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

doi:10.1002/chem.201200431

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 journal › Journal article › Research › peer-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 sp^2-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 language	English
Journal	Chemistry-a European Journal
Volume	18
Issue number	28
Pages (from-to)	8774-8779
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.201200431
Publication status	Published - 2012
Externally published	Yes

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@article{d8ae31f095ae4f5abecd39dae2e7708c,

title = "Palladium-Catalysed Cross-Coupling of Vinyldisiloxanes with Benzylic and Allylic Halides and Sulfonates",

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.",

author = "Frye, {Elizabeth C.} and O'Connor, {Cornelius J.} and Twigg, {David G.} and Bryony Elbert and Luca Laraia and Hulcoop, {David G.} and Venkitaraman, {Ashok R.} and Spring, {David R.}",

year = "2012",

doi = "10.1002/chem.201200431",

language = "English",

volume = "18",

pages = "8774--8779",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "28",

}

Palladium-Catalysed Cross-Coupling of Vinyldisiloxanes with Benzylic and Allylic Halides and Sulfonates. / Frye, Elizabeth C.; O'Connor, Cornelius J.; Twigg, David G.; Elbert, Bryony; Laraia, Luca; Hulcoop, David G.; Venkitaraman, Ashok R.; Spring, David R.

In: Chemistry-a European Journal, Vol. 18, No. 28, 2012, p. 8774-8779.

Research output: Contribution to journal › Journal article › Research › peer-review

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 -