Selective Iodosulfonylation of Allenes

Selective Iodosulfonylation of Allenes

Author: ChemistryViews.org

Allenes are reactive molecules that can be used in a variety of difunctionalization reactions to give useful synthetic intermediates. However, performing these reactions in a regioselective manner can be challenging.

Zhiguo Zhang, Guisheng Zhang, and colleagues, Henan Normal University, China, have developed a highly regioselective iodosulfonylation of allenes to give (E)-α-iodomethyl vinylsulfones (pictured). The team used sulfonyl iodides as combined iodine and sulfonyl sources, copper(I) iodide as a catalyst, and 1,10-phenanthroline as a ligand in dichloromethane (DCM) at room temperature.

The reaction gives the desired vinylsulfones in moderate to excellent yields and with high regio- and stereoselectivity and tolerates a range of functional groups. The researchers suggest that the reaction proceeds via a free-radical pathway. Both the allylic halide and the vinylsulfone group can be further transformed, which makes the products useful building blocks for organic synthesis.


 

Leave a Reply

Your email address will not be published.