4.4 Article

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

Journal

TETRAHEDRON
Volume 73, Issue 29, Pages 4052-4061

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.12.002

Keywords

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

Funding

  1. National Institutes of Health [GM116031]
  2. ACS Petroleum Research Fund [54831-DNI1]
  3. NSF [CHE- 0234811, CHE-0840509]

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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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