4.6 Article

Manganese-catalyzed chlorosulfonylation of terminal alkene and alkyne via convergent paired electrolysis

Journal

CELL REPORTS PHYSICAL SCIENCE
Volume 2, Issue 7, Pages -

Publisher

CELL PRESS
DOI: 10.1016/j.xcrp.2021.100476

Keywords

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Funding

  1. National Natural Science Foundation of China [22031008]
  2. Science Foundation of Wuhan [2020010601012192]

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This method utilizes manganese salt as a catalyst and redox mediator to achieve a successful radical addition reaction of terminal aryl alkenes and alkynes with sulfonyl chlorides in organic synthesis, producing highly selective products.
Convergent paired electrolysis is an energy-efficient model in organic synthesis, although the main obstacle with its use is matching properties of the intermediates generated in two electrodes. With the development of anodic-coupled electrosynthesis in three-component difunctionalization of alkene, a proposal for two-component difunctionalization of alkene and alkyne using a difunctional reagent has been raised. Herein, we develop a manganese-catalyzed, atom-transfer radical addition of the terminal aryl alkenes and alkynes with sulfonyl chlorides, in which manganese salt has the role of a chlorine atom-transfer catalyst as well as a redox mediator. This method generates analogs of chlorosulfonylated products of high regio- and stereoselectivity, which are derivatives of pharmaceutical drugs and natural products.

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