Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Liam T. Ball; Michael Green; Guy C. Lloyd-Jones; Christopher A. Russell

doi:10.1021/ol1019162

Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Liam T. Ball, Michael Green, Guy C. Lloyd-Jones^*, Christopher A. Russell

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract / Description of output

Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph(3)PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.

Original language	English
Pages (from-to)	4724-4727
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol1019162
Publication status	Published - 5 Nov 2010

Keywords / Materials (for Non-textual outputs)

CROSS-COUPLING REACTIONS
C BOND FORMATION
HETEROGENEOUS CATALYSTS
NONACTIVATED ARENES
COMPLEXES
ARYL
AMINATION
GOLD(III)
LIGANDS
HALIDES

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@article{4a69e919034e41148df80853409c0b6f,

title = "Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes",

abstract = "Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph(3)PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.",

keywords = "CROSS-COUPLING REACTIONS, C BOND FORMATION, HETEROGENEOUS CATALYSTS, NONACTIVATED ARENES, COMPLEXES, ARYL, AMINATION, GOLD(III), LIGANDS, HALIDES",

author = "Ball, {Liam T.} and Michael Green and Lloyd-Jones, {Guy C.} and Russell, {Christopher A.}",

year = "2010",

month = nov,

day = "5",

doi = "10.1021/ol1019162",

language = "English",

volume = "12",

pages = "4724--4727",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Arylsilanes

T2 - Application to Gold-Catalyzed Oxyarylation of Alkenes

AU - Ball, Liam T.

AU - Green, Michael

AU - Lloyd-Jones, Guy C.

AU - Russell, Christopher A.

PY - 2010/11/5

Y1 - 2010/11/5

N2 - Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph(3)PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.

AB - Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph(3)PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.

KW - CROSS-COUPLING REACTIONS

KW - C BOND FORMATION

KW - HETEROGENEOUS CATALYSTS

KW - NONACTIVATED ARENES

KW - COMPLEXES

KW - ARYL

KW - AMINATION

KW - GOLD(III)

KW - LIGANDS

KW - HALIDES

U2 - 10.1021/ol1019162

DO - 10.1021/ol1019162

M3 - Article

SN - 1523-7060

VL - 12

SP - 4724

EP - 4727

JO - Organic letters

JF - Organic letters

IS - 21

ER -

Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Abstract / Description of output

Keywords / Materials (for Non-textual outputs)

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