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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 trifluoromethanesulfonic acid to provide the corresponding 2‐amino‐2′‐sulfanyl‐ and/or 4‐amino‐4′‐sulfanylbiphenyls. Mechanistic studies indicate that the C−C‐bond‐forming sigmatropic rearrangement proceeds intramolecularly from dicationic S−N‐tethered species. [ABSTRACT FROM AUTHOR]

Aryl sulfoxides underwent dehydrogenative coupling with unprotected anilines under Pummerer-type conditions to provide the corresponding 2-amino-2'-sulfanyl-and/or 4-amino-4'-sulfanylbiphenyls. Aryl sulfoxides underwent dehydrogenative coupling with unprotected anilines under Pummerer-type conditions to provide the corresponding 2-amino-2'-sulfanyl-and/or 4-amino-4'-sulfanylbiphenyls. [Extracted from the article]