Electrocatalytic Enantioselective Tandem C–H Indolization toward Biindolyl Atropisomers: Reaction Development and Mechanistic Insight
The electrochemical methods for asymmetric indolization are still elusive and pose a significant challenge. Taking advantage of 2-alkynylanilines as electrochemically compatible indolyl equivalents, we herein represent a mild and highly enantioselective electrocatalytic process for tandem C–H indolization to form 2,3′-biindolyl atropisomers along with hydrogen evolution reaction. Integrated experimental and computational mechanistic studies revealed that a sequential C–H metalation/nucleophilic cyclization/reductive elimination/anodic oxidation sequence involving a RhIII–RhI–RhIII catalytic cycle accounts for the established transformation.
Authors
- Zhongyi Zeng (ORCID: https://orcid.org/0000-0003-3366-7592)
- Zhi‐Huan Peng
- Ao-Long Li (ORCID: https://orcid.org/0009-0003-6660-8887)
- Shengdong Wang (ORCID: https://orcid.org/0000-0001-7431-2515)
- Zhi Zhou (ORCID: https://orcid.org/0000-0002-6521-8946)
- Hui Gao (ORCID: https://orcid.org/0000-0002-8736-4485)
- Ping Huang (ORCID: https://orcid.org/0000-0003-1683-909X)
- Wei Yi (ORCID: https://orcid.org/0000-0001-7936-9326)
- Jiating Cai
- Yuanyuan Li (ORCID: https://orcid.org/0000-0003-2155-0901)
- Qin Shi (ORCID: https://orcid.org/0000-0002-9403-752X)
- Zhikang Li (ORCID: https://orcid.org/0000-0002-6076-4913)
- Mingkai Yang
Institutions
- State Key Laboratory of Respiratory Disease (CN)
- Guangzhou Medical University (CN)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2025-01-09
- DOI
- https://doi.org/10.1021/acscatal.4c06594
- Citations
- 5
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Basic and Applied Basic Research Foundation of Guangdong Province