Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C–H and C–NO<sub>2</sub> Bond Activations
A general approach for the α-arylation of heteroarenes with nitroarenes via denitrative coupling is reported for the first time. Various heteroarenes, including derivatives of furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at the α-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C-H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.
Authors
- Yuxuan Xiao (ORCID: https://orcid.org/0000-0002-7332-6568)
- Lin Yu (ORCID: https://orcid.org/0000-0002-1668-4422)
- Xun Yang (ORCID: https://orcid.org/0000-0003-2113-5839)
- Jiaxin Yao (ORCID: https://orcid.org/0000-0003-2419-6928)
- Haiyan Li (ORCID: https://orcid.org/0000-0001-8022-3447)
- Feng Lin (ORCID: https://orcid.org/0000-0002-3729-3148)
- Wengui Duan (ORCID: https://orcid.org/0000-0001-8140-0011)
- Ying Yin (ORCID: https://orcid.org/0000-0003-2156-4588)
- Jiahui Du (ORCID: https://orcid.org/0000-0003-3082-6826)
Institutions
- Guangxi University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-22
- DOI
- https://doi.org/10.1021/acs.orglett.4c02340
- Citations
- 14
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- Guangxi University
- Specific Research Project of Guangxi for Research Bases and Talents