Ketyl radical reactivity via atom transfer catalysis

  • Lu Wang
    Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
  • Jeremy M. Lear
    Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
  • Sean M. Rafferty
    Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
  • Stacy C. Fosu
    Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
  • David A. Nagib
    Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.

書誌事項

公開日
2018-10-12
DOI
  • 10.1126/science.aau1777
公開者
American Association for the Advancement of Science (AAAS)

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説明

<jats:title>Iodine smooths the way to ketyl radicals</jats:title> <jats:p> Chemists typically transform carbonyl compounds through polar two-electron reactions. It is also possible to pursue radical coupling strategies by adding just one electron to form a ketyl group. However, the strong reductant supplying that electron often limits the reaction's versatility. Wang <jats:italic>et al.</jats:italic> report a mild means of forming ketyls by first adding acetyl iodides across the C=O bond (see the Perspective by Blackburn and Roizen). A photoactivated manganese catalyst then temporarily pulls the iodine away, leaving a ketyl to couple with alkynes. The iodine then returns to one of the alkyne's carbons, stabilizing the product but remaining poised for further transformations. </jats:p> <jats:p> <jats:italic>Science</jats:italic> , this issue p. <jats:related-article xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="doi" issue="6411" page="225" related-article-type="in-this-issue" vol="362" xlink:href="10.1126/science.aau1777">225</jats:related-article> ; see also p. <jats:related-article xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="doi" issue="6411" page="157" related-article-type="in-this-issue" vol="362" xlink:href="10.1126/science.aav0574">157</jats:related-article> </jats:p>

収録刊行物

  • Science

    Science 362 (6411), 225-229, 2018-10-12

    American Association for the Advancement of Science (AAAS)

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