Bis(sulfonyl)methyl Insertion into Alkenyl versus Phenyl Carbon−Hydrogen Bonds in the Reaction of Bis(sulfonyl)iodonium Ylides with Highly Phenylated Ethylenes

The reaction of bis(sulfonyl)iodonium ylides α − γ with triphenylethylene ( 2a ) and tetraphenylethylene ( 2b ) affords insertion products into the alkenyl and phenyl carbon−hydrogen bonds of the substrate. A mechanistically perplexing feature is the diversity displayed in the reactivity pattern of the bis(sulfonyl)iodonium ylides in their reaction with the phenylated alkenes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)