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

作者：Asgari Parham; Dakarapu Udaya Sree; Nguyen Hiep H; Jeon Junha^*

来源：Tetrahedron, 2017, 73(29): 4052-4061.

DOI：10.1016/j.tet.2016.12.002

• Aryne
• Arrylsilyl triflates
• Benzodioxasilines
• C-H activation
• Cycloaddition
• Silyl acetals

Diversely substituted arylsilyl triflates, as aryne precursors for aryne cycloaddition reactions, were accessed from benzodioxasilines. Catalytic reductive C-H 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.

• 出版日期2017-7-20