beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes

Michael Weller; Benson Kariuki; Liam Cox

doi:10.1016/j.tetlet.2008.05.081

beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes

Michael Weller
, Benson Kariuki
, Liam Cox

Chemistry

Research output: Contribution to journal › Article

8 Citations (Scopus)

Abstract

A stereoselective haloclestannylation of (E)-beta-stannylvinyisilane 6 has been used to access a range of (E)-beta-halovinylsilanes. Most notably, the beta-fluorovinylsilane 14 was accessed in high yield using the Select-fluor (R) reagent, and subsequently converted into a masked hexayne 22. Release of the hexayne 25 was achieved by exposing 22 to sub-stoichiometric quantities of fluoride. (c) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4596-4600
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.081
Publication status	Published - 1 Jan 2008

Keywords

tin-halogen exchange
vinylsilanes
oligoynes
polyynes
beta-elimination

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10.1016/j.tetlet.2008.05.081

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title = "beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes",

abstract = "A stereoselective haloclestannylation of (E)-beta-stannylvinyisilane 6 has been used to access a range of (E)-beta-halovinylsilanes. Most notably, the beta-fluorovinylsilane 14 was accessed in high yield using the Select-fluor (R) reagent, and subsequently converted into a masked hexayne 22. Release of the hexayne 25 was achieved by exposing 22 to sub-stoichiometric quantities of fluoride. (c) 2008 Elsevier Ltd. All rights reserved.",

keywords = "tin-halogen exchange, vinylsilanes, oligoynes, polyynes, beta-elimination",

author = "Michael Weller and Benson Kariuki and Liam Cox",

year = "2008",

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day = "1",

doi = "10.1016/j.tetlet.2008.05.081",

language = "English",

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pages = "4596--4600",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes

AU - Weller, Michael

AU - Kariuki, Benson

AU - Cox, Liam

PY - 2008/1/1

Y1 - 2008/1/1

N2 - A stereoselective haloclestannylation of (E)-beta-stannylvinyisilane 6 has been used to access a range of (E)-beta-halovinylsilanes. Most notably, the beta-fluorovinylsilane 14 was accessed in high yield using the Select-fluor (R) reagent, and subsequently converted into a masked hexayne 22. Release of the hexayne 25 was achieved by exposing 22 to sub-stoichiometric quantities of fluoride. (c) 2008 Elsevier Ltd. All rights reserved.

AB - A stereoselective haloclestannylation of (E)-beta-stannylvinyisilane 6 has been used to access a range of (E)-beta-halovinylsilanes. Most notably, the beta-fluorovinylsilane 14 was accessed in high yield using the Select-fluor (R) reagent, and subsequently converted into a masked hexayne 22. Release of the hexayne 25 was achieved by exposing 22 to sub-stoichiometric quantities of fluoride. (c) 2008 Elsevier Ltd. All rights reserved.

KW - tin-halogen exchange

KW - vinylsilanes

KW - oligoynes

KW - polyynes

KW - beta-elimination

U2 - 10.1016/j.tetlet.2008.05.081

DO - 10.1016/j.tetlet.2008.05.081

M3 - Article

VL - 49

SP - 4596

EP - 4600

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes

Abstract

Keywords

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