Regiospecific Synthesis of Aryl(2-furyl)iodonium Tosylates, a New Class of Iodonium Salts, from arenes and 2-(Trimethylsilyl)furans in Organic Solvents
The treatment of 2,5-bis(trimethylsilyl)furan with various arenes (ArI(OH)OTs) in acetonitrile/ methanol has been found to give aryliodonium tosylates in yields ranging from 62percent to 80percent.With 2-methyl-5-(trimethylsilyl)furan as the substrate, aryl(5-methyl-2-furyl)iodonium tosylates are likewise obtained in yields ranging from 61percent to 74percent.The reactions of arenes with 2-(trimethylsilyl)furan in methanol give aryl(2-furyl)iodonium tosylates in much lower yield (9-23percent) and are accompanied by the reductive decomposition of the hypervalent organoiodine component.To our knowledge, these are the first reported examples of aryl(furyl)iodonium salts.
Carman, Carol S.,Koser, Gerald F.
p. 2534 - 2539
(2007/10/02)
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