38452-17-4Relevant articles and documents
Construction of Biaryls from Aryl Sulfoxides and Anilines by Means of a Sigmatropic Rearrangement
Yanagi, Tomoyuki,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 783 - 787 (2019/11/13)
An unprecedented S?N variant of the benzidine rearrangement for construction of biaryls has been developed. Aryl sulfoxides underwent dehydrogenative coupling with anilines by successive treatment with trifluoromethanesulfonic anhydride and trifluorometha
Metal-Free Approach to Biaryls from Phenols and Aryl Sulfoxides by Temporarily Sulfur-Tethered Regioselective C-H/C-H Coupling
Yanagi, Tomoyuki,Otsuka, Shinya,Kasuga, Yuko,Fujimoto, Keisuke,Murakami, Kei,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 14582 - 14585 (2016/11/18)
We have developed metal-free regiocontrolled dehydrogenative C-H/C-H cross-coupling of aryl sulfoxides with phenols by means of trifluoroacetic anhydride. Because the reaction would proceed through an interrupted Pummerer reaction followed by sulfonium-tethered [3,3]-sigmatropic rearrangement, the C-H/C-H coupling takes place exclusively between the ortho positions of both substrates. Various functional groups including carbonyl, halo, siloxy, and even boryl moieties are compatible. The biaryl products naturally possess hydroxy and sulfanyl groups, which allows the products to be useful synthetic intermediates, as evidenced by the syntheses of π-expanded heteroarenes such as unprecedented 7,12-dioxa[8]helicene.