Site‐Selective Alkenylation of Unactivated C(sp<sup>3</sup>)−H Bonds Mediated by Compact Sulfate Radical

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  • Mitsuhiro Ueda
    Department of Chemistry Graduate School of Science Osaka Prefecture University Sakai Osaka 599-8531 Japan
  • Kazuya Kamikawa
    Department of Chemistry Graduate School of Science Osaka Prefecture University Sakai Osaka 599-8531 Japan
  • Takahide Fukuyama
    Department of Chemistry Graduate School of Science Osaka Prefecture University Sakai Osaka 599-8531 Japan
  • Yi‐Ting Wang
    Department of Applied Chemistry National Chiao Tung University Hsinchu Taiwan
  • Yen‐Ku Wu
    Department of Applied Chemistry National Chiao Tung University Hsinchu Taiwan
  • Ilhyong Ryu
    Department of Chemistry Graduate School of Science Osaka Prefecture University Sakai Osaka 599-8531 Japan

書誌事項

公開日
2020-12-14
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/ange.202011992
  • 10.1002/anie.202011992
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site‐selective alkenylation of unactivated C(sp<jats:sup>3</jats:sup>)−H bonds with 1,2‐bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes (<jats:italic>E</jats:italic>)‐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.</jats:p>

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