Diaryliodonium salts have long been recognized as potent arylating agents of various nucleophiles under mild conditions as well as highly active aryl donors in metal catalyzed cross-coupling reactions.  Recently in our laboratory we have prepared a novel series of diaryliodonium betaines by the treatment of 1H-1-hydroxy-1,2,3-benziodoxathiole 3,3-dioxide with various electron rich to moderately electron poor arenes in 2,2,2-triflouroethanol under ambient conditions and explored the suitability of these compounds as aryl donors in Suzuki-Miyaura and other metal-catalzed cross coupling reactions.  Similar to previously investigated diaryliodonium salts the most electron rich aryl ring is preferentially transferred.  However, the advantage of these betaines lies in the simplification of the reaction mixture.  The reduced 2-iodobenzenesulfonate by-product is readily removed in the initial aqueous extraction of the reaction mixture and can be isolated and reused with high efficiency.

Metal catalyzed arylation reactions using 2-[(Aryl)iodonio]benzenesulfonates

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.