Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization
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 interm...
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sg-ntu-dr.10356-1497252023-02-28T19:57:10Z Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization Cheng, Jian Sun, Jun Yan, Jiekuan Yang, Song Zheng, Pengcheng Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Functionalization Catalysts 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. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version 2021-06-02T06:09:15Z 2021-06-02T06:09:15Z 2017 Journal Article 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. https://dx.doi.org/10.1021/acs.joc.7b02436 1520-6904 https://hdl.handle.net/10356/149725 10.1021/acs.joc.7b02436 29131620 2-s2.0-85038442286 24 82 13342 13347 en Journal of Organic Chemistry 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 https://doi.org/10.1021/acs.joc.7b02436 application/pdf |
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Science::Chemistry Functionalization Catalysts Cheng, Jian Sun, Jun Yan, Jiekuan Yang, Song Zheng, Pengcheng Jin, Zhichao Chi, Robin Yonggui Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| description |
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. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Cheng, Jian Sun, Jun Yan, Jiekuan Yang, Song Zheng, Pengcheng Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Cheng, Jian Sun, Jun Yan, Jiekuan Yang, Song Zheng, Pengcheng Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Cheng, Jian |
| title |
Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| title_short |
Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| title_full |
Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| title_fullStr |
Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| title_full_unstemmed |
Carbene-catalyzed indole 3-methyl C(sp3)-H bond functionalization |
| title_sort |
carbene-catalyzed indole 3-methyl c(sp3)-h bond functionalization |
| publishDate |
2021 |
| url |
https://hdl.handle.net/10356/149725 |
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1759854383694086144 |