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

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

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...

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Bibliographic Details
Main Authors: Yamakawa, Takeshi, Yoshikai, Naohiko, Wong, Mun Yee
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Online Access:https://hdl.handle.net/10356/107215
http://hdl.handle.net/10220/25309
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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