Synthesis of Programmable Tetra-ortho-Substituted Biaryl Compounds Using Diels−Alder Cycloadditions/Cycloreversions of Disubstituted Alkynyl Stannanes

Johanna R. Perkins and Rich G. Carter*
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331
J. Am. Chem. Soc., 2008, 130 (11), pp 3290–3291
DOI: 10.1021/ja7113486
Publication Date (Web): February 26, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rich.carter@oregonstate.edu

Abstract

Abstract Image

Orthogonally functionalized, programmable biaryl templates have been synthesized utilizing aryl acetylenic stannanes and oxygenated dienes in a cycloaddition/cycloreversion strategy. Sequential functionalization of each of the four ortho positions has been demonstrated. Subsequent resolution of a representative anilino phenol has been accomplished. Additionally, a highly active anhydrous, boroxine-based Suzuki coupling protocol has been developed for conversion of unreactive aryl chlorides.

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History

  • Published In Issue March 19, 2008
  • Received December 28, 2007

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