Tandem reactions involving 1-silyl-3-boryl-2-alkenes. New access to (Z)-1-fluoro-1-alkenes, allyl fluorides, and diversely α-substituted allylboronates. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2013

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

Résumé

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

hal-00787405 , version 1 (12-02-2013)

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Aurélie Macé, Fabien Tripoteau, Qian Zhao, Eric Gayon, Emmanuel Vrancken, et al.. Tandem reactions involving 1-silyl-3-boryl-2-alkenes. New access to (Z)-1-fluoro-1-alkenes, allyl fluorides, and diversely α-substituted allylboronates.. Organic Letters, 2013, 15 (4), pp.906-9. ⟨10.1021/ol4000263⟩. ⟨hal-00787405⟩
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