Site-Selective Alkenylation of Unactivated C(sp )-H Bonds Mediated by Compact Sulfate Radical.

Angew Chem Int Ed Engl

Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka, 599-8531, Japan.

Published: February 2021

AI Article Synopsis

  • A new method allows the selective alkenylation of unactivated C(sp)–H bonds using 1,2-bis(phenylsulfonyl)ethene and persulfate, resulting in high yields of (E)-2-alkylvinylphenylsulfones.
  • This technique is effective for a wide range of substrates, including those with sterically hindered C-H bonds, which were previously challenging to target.
  • The improved efficacy is due to the small size of the sulfate radical used in the activation process, allowing for greater versatility in the types of compounds that can be modified.

Article Abstract

A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site-selective alkenylation of unactivated C(sp )-H bonds with 1,2-bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes (E)-2-alkylvinylphenylsulfones in up to 88 % yield. In contrast with the previously reported decatungstate protocol, the current method is applicable to alkenylation of sterically hindered C-H bonds. This important advantage significantly broadens the substrate scope, and is attributed to the compact size of the sulfate radical employed in the C-H activation and cleavage.

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Source
http://dx.doi.org/10.1002/anie.202011992DOI Listing

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