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

Weller, Michael D., Kariuki, Benson and Cox, Liam R. 2008. beta-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from beta-fluorovinylsilanes. Tetrahedron Letters 49 (31) , pp. 4596-4600. 10.1016/j.tetlet.2008.05.081

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Vinylsilanes; Oligoynes; Polyynes; β-Elimination; Tin–halogen exchange
Publisher: Elsevier
ISSN: 0040-4039
Last Modified: 04 Jun 2017 03:42
URI: http://orca-mwe.cf.ac.uk/id/eprint/25060

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