Rhodium(II)-Catalyzed Divergent Dearomative Cyclization of 1,3-Azoles with Cyclopropenes
Abstract Herein, we report a rhodium(II)-catalyzed divergent dearomative cyclization of benzimidazoles and benzoxazoles with cyclopropenes that proceeds through a unified azolium ylide mechanism. Scaffold tuning of the 1,3-azole substrates enables two distinct pathways: pyrroloimidazoles from benzimidazoles and benzoxazoloazepines from benzoxazoles. This method features good functional group tolerance and gram-scale scalability, providing straightforward access to two classes of pharmaceutically relevant nitrogen heterocycles.
Authors
- Nengzhong Wang (ORCID: https://orcid.org/0000-0003-1690-7611)
- Hui Qin Yao (ORCID: https://orcid.org/0000-0002-4450-8602)
- Nianyu Huang (ORCID: https://orcid.org/0000-0003-4483-160X)
- Xinyu Liu (ORCID: https://orcid.org/0000-0003-0854-8559)
- Linxuan Li (ORCID: https://orcid.org/0000-0001-9836-1442)
- Shuai Ma (ORCID: https://orcid.org/0000-0003-3452-1739)
- Yuan-Qing Dong
- Meiling Dai
Institutions
- China Three Gorges University (CN)
- Art Innovation (Netherlands) (NL)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-08-20
- DOI
- https://doi.org/10.1021/acs.orglett.6c03156
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hubei Provincial Department of Education
- National Natural Science Foundation of China
- Natural Science Foundation of Hubei Province
- Higher Education Discipline Innovation Project