Carbene-Catalyzed Indole 3-Methyl C(sp3)-H Bond Functionalization

Jian Cheng; Jun Sun; Jiekuan Yan; Song Yang; Pengcheng Zheng; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acs.joc.7b02436

Carbene-Catalyzed Indole 3-Methyl C(sp³)-H Bond Functionalization

Jian Cheng, Jun Sun, Jiekuan Yan, Song Yang^*, Pengcheng Zheng, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

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.

Original language	English
Pages (from-to)	13342-13347
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.7b02436
Publication status	Published - Dec 15 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Organic Chemistry

Access to Document

10.1021/acs.joc.7b02436

Cite this

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title = "Carbene-Catalyzed Indole 3-Methyl C(sp3)-H Bond Functionalization",

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.",

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AU - Cheng, Jian

AU - Sun, Jun

AU - Yan, Jiekuan

AU - Yang, Song

AU - Zheng, Pengcheng

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2017/12/15

Y1 - 2017/12/15

N2 - 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.

AB - 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.

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