Hypervalent Iodine(III)-Catalysis Using Sulfoxide Oxidant for the Dehydrogenative Cycloisomerization-Arylation Reaction of 2-Propargyl 1,3-Dicarbonyl Compounds

We report herein an unprecedented hypervalent iodine(III)-catalysis using the activated sulfoxide. Since the present catalytic systems promote the dehydrogenative cycloisomerization-arylation reaction of 2-propargyl 1,3-dicarbonyl compounds with aromatics, this report also provides one of the few methods for iodine(III)-catalyzed intermolecular carbon-carbon bond formation of aromatics. Hypervalent iodine(III) catalysis using an activated sulfoxide as a terminal oxidant has been developed for the metal-free synthesis of arylated furans. o-Nitrobenzenesulfonyl chloride (o-NsCl) or the generated acid activates the sulfoxide. 1-(Chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium 4-methylbenzenesulfonate (TEDA-OTs) contributes to the stability of the activated sulfoxide. image