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      Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes

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      Author
      Wong, Mun Yee
      Yamakawa, Takeshi
      Yoshikai, Naohiko
      Date of Issue
      2015
      School
      School of Physical and Mathematical Sciences
      Version
      Accepted version
      Abstract
      An iron–N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C–H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C–H bond to the iron center, insertion of the unsaturated bond into the Fe–H bond, and C–C reductive elimination.
      Subject
      DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
      Type
      Journal Article
      Series/Journal Title
      Organic letters
      Rights
      © 2015 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Letters, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/ol503395g].
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      http://dx.doi.org/10.1021/ol503395g
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