Selective Iodosulfonylation of Allenes

  • Author: ChemistryViews.org
  • Published: 15 July 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Selective Iodosulfonylation of Allenes

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.


 

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