Direct C−C Bond Cleavage of CH<sub>3</sub>CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐<i>a</i>]quinoxalines <i>via</i> Electrochemical Oxidation
Abstract A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐ a ]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH 3 CN has been developed, which includes the functionalization of C( sp 3 )−H bonds as well as the construction of C−C and C−N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH 3 CN in this reaction acts as both a carbon source via C−C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐ a ]quinoxaline derivatives were obtained.
Authors
- Man Miao
- Zhenyu An (ORCID: https://orcid.org/0000-0002-1595-2077)
- Jianqiang Yu
- Xiao‐Bing Lan (ORCID: https://orcid.org/0000-0001-5301-069X)
- Jian Zhang (ORCID: https://orcid.org/0000-0002-6558-791X)
- Wenxue Li (ORCID: https://orcid.org/0000-0002-7308-7827)
- Fengkai Sun (ORCID: https://orcid.org/0000-0003-1492-3474)
Institutions
- Shanghai Jiao Tong University (CN)
- Ningxia Medical University (CN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-08-19
- DOI
- https://doi.org/10.1002/adsc.202400886
- Citations
- 6
- Primary Topic
- Synthesis and Biological Evaluation
- Type
- article
- Field-Weighted Citation Impact
- 1.50