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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. doi:10.1021/acs.joc.7b02436
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: 0022-3263
DOI: 10.1021/acs.joc.7b02436
Rights: © 2017 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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