Tetrahedron
Tetrahedron
5 years ago

Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-CH silylation of phenols with traceless acetal directing groups

Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-CH silylation of phenols with traceless acetal directing groups
Diversely substituted arylsilyl triflates, as aryne precursors for aryne cycloaddition reactions, were accessed from benzodioxasilines. Catalytic reductive CH ortho-silylation of phenols with traceless acetal directing groups was exploited to prepare benzodioxasilines. Sequential addition of MeLi and then trifluoromethanesulfonic anhydride to benzodioxasilines provided arylsilyl triflates in a single pot. Notably, this approach was successfully utilized to prepare sterically hindered 1,2,3-trisubstituted arylsilyl triflates, which ultimately underwent fluoride-mediated aryne cycloaddition.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402016312698

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