Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/107215
Title: Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes
Authors: Yamakawa, Takeshi
Yoshikai, Naohiko
Wong, Mun Yee
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Issue Date: 2015
Source: Wong, M. Y., Yamakawa, T., & Yoshikai, N. (2015). Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes. Organic letters, 17(3), 442-445.
Series/Report no.: Organic letters
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.
URI: https://hdl.handle.net/10356/107215
http://hdl.handle.net/10220/25309
DOI: 10.1021/ol503395g
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].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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