Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes
Author
Wong, Mun Yee
Yamakawa, Takeshi
Yoshikai, Naohiko
Date of Issue
2015School
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].
Collections
http://dx.doi.org/10.1021/ol503395g
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