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Title: Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization
Authors: Cheng, Jian
Sun, Jun
Yan, Jiekuan
Yang, Song
Zheng, Pengcheng
Jin, Zhichao
Chi, Robin Yonggui
Keywords: Science::Chemistry
Issue Date: 2017
Source: Cheng, J., Sun, J., Yan, J., Yang, S., Zheng, P., Jin, Z. & Chi, R. Y. (2017). Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization. Journal of Organic Chemistry, 82(24), 13342-13347.
Journal: Journal of Organic Chemistry
Abstract: The metal-free catalytic functionalization of aromatic sp2-carbons and benzylic sp3-carbons remains challenging. Here we report a carbene-catalyzed functionalization of the 3-methyl sp3-carbon attached to 2-formyl-indoles. The reaction proceeds through an NHC-bound o-quinodimethane as the key intermediate generated from 2-formyl-3-methylindoles under oxidative conditions. Reactive ketones are found to be effective substrates to produce substituted hydropyrano[3,4-b]indoles in good to excellent yields.
ISSN: 1520-6904
DOI: 10.1021/acs.joc.7b02436
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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