Palladium-Catalyzed Dearomative Heck/C(sp<sup>2</sup>)–H Activation/Decarboxylative Cyclization of C2-Tethered Indoles
Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture of the transient alkyl-Pd(II) species. Herein, we disclose a novel palladium-catalyzed dearomative Heck/C(sp<sup>2</sup>)-H activation/decarboxylative cyclization of C2-tethered indoles. In this protocol, the alkyl-Pd(II) species formed by dearomatization of C2-tethered indoles is not terminated by common β-H elimination or nucleophilic capture, but rather generates <i>C</i>,<i>C</i>-palladacycle via C-H activation. The latter is intercepted by α-bromoacrylic acids to produce pentacyclic and heptacyclic fused indolines.
Authors
- Yun Teh S. Liang (ORCID: https://orcid.org/0000-0002-2550-9220)
- Shuyi Guo (ORCID: https://orcid.org/0000-0001-7860-0661)
- Yuan Yang (ORCID: https://orcid.org/0000-0002-9061-1758)
- Ji‐Bao Xia (ORCID: https://orcid.org/0000-0002-2262-5488)
- Wenbo Deng
- Xing Yang (ORCID: https://orcid.org/0009-0002-3031-6746)
- Xiaochang Xiao
Institutions
- Hunan Normal University (CN)
- Ministry of Education (BD)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-21
- DOI
- https://doi.org/10.1021/acs.orglett.4c03663
- Citations
- 7
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- Education Department of Hunan Province
- National Natural Science Foundation of China
- Natural Science Foundation of Hunan Province
- Training Program for Excellent Young Innovators of Changsha