Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/102755
Title: Alkene isomerization-hydroarylation tandem catalysis : indole C2-alkylation with aryl-substituted alkenes leading to 1,1-diarylalkanes
Authors: Yoshikai, Naohiko
Yamakawa, Takeshi
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Issue Date: 2014
Source: Yamakawa, T., & Yoshikai, N. (2014). Alkene isomerization-hydroarylation tandem catalysis : indole C2-alkylation with aryl-substituted alkenes leading to 1,1-diarylalkanes. Chemistry - An Asian Journal, in press.
Series/Report no.: Chemistry - an Asian journal
Abstract: A cobalt-N-heterocyclic carbene catalyst generated from CoBr2, imidazolium salt, and cyclohexylmagnesium bromide was found to promote the imine-directed C2-alkylation of indoles with nonconjugated arylalkenes through a tandem alkene isomerization–hydroarylation process, affording 1,1-diarylalkanes with exclusive regioselectivity. The feasibility of the tandem catalysis was demonstrated for allyl-, homoallyl-, and bishomoallylbenzene derivatives. The catalytic system is also applicable to a variety of β-substituted styrene derivatives. Mechanistic experiments using deuterium-labeled indole substrate and Grignard reagent provided insight into the cobalt-mediated C[BOND]H activation step, which likely involves exchange of the C2-hydrogen atom of the former and the β-hydrogen atoms of the latter.
URI: https://hdl.handle.net/10356/102755
http://hdl.handle.net/10220/19125
ISSN: 1861-4728
DOI: 10.1002/asia.201400135
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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