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American Chemical Society, Organic Letters, 4(15), p. 906-909, 2013

DOI: 10.1021/ol4000263

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Tandem reactions involving 1-silyl-3-boryl-2-alkenes. New access to (Z)-1-fluoro-1-alkenes, allyl fluorides, and diversely α-substituted allylboronates.

Journal article published in 2013 by Aurélie Macé ORCID, Fabien Tripoteau, Qian Zhao, Eric Gayon, Emmanuel Vrancken, Jean-Marc Campagne, Bertrand Carboni
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The reactions of 1-silyl-3-boryl-2-alkenes with various electrophilic reagents (Selecffluor, N-halosuccinimides, benzhydryl, and propargylic alcohols In the presence of a Lewis acid, N-alkoxycarbonyliminium ion) have been investigated as new routes to alpha-substituted allylboronates. Further functional transformations, including allylboration, Suzuki coupling, protodeboronation, and cycloisomerization, have been carried out to illustrate the synthetic potential of these gamma-borylallylsilanes.