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Copper-Catalyzed Difunctionalization of Allenes with Sulfonyl Iodides Leading to (E)‑α-Iodomethyl Vinylsulfones

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journal contribution
posted on 09.07.2018 by Ning Lu, Zhiguo Zhang, Nana Ma, Conghui Wu, Guisheng Zhang, Qingfeng Liu, Tongxin Liu
A highly regioselective iodosulfonylation of allenes in the presence of CuI and 1,10-phenanthroline has been developed for the synthesis of various useful (E)-α-iodomethyl vinylsulfones in moderate to excellent yields. This practical reaction is fast, operationally simple, and in particular, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity. The selectivity was illustrated by a conceptual DFT analysis.