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

TETRAHEDRON

卷:73

Article

Asgari, Parham¹  Dakarapu, Udaya Sree¹  Nguyen, Hiep H.¹  Jeon, Junha¹ 

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

关键词: Aryne;    Arrylsilyl triflates;    Benzodioxasilines;    C-H activation;    Cycloaddition;    Silyl acetals;   

DOI  :  10.1016/j.tet.2016.12.002

来源: Elsevier

【 摘 要 】

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. (C) 2016 Elsevier Ltd. All rights reserved.

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