Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds
A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly of densely functionalized indoles. This new catalytic process represents the first example of a cascade intramolecular nucleophilic cyclization by the N-H insertion of amines. Various naphthylamines and α-diazocarbonyl compounds could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to novel heterocyclic analogues not easily accessible by other methods.
Authors
- Xiaogang Wang (ORCID: https://orcid.org/0000-0001-5938-1141)
- Di Chen (ORCID: https://orcid.org/0000-0002-1303-8038)
- Chengfang Qiao (ORCID: https://orcid.org/0000-0001-7411-7306)
- Michal Szostak (ORCID: https://orcid.org/0000-0002-9650-9690)
- Yishou Wang (ORCID: https://orcid.org/0000-0001-8043-843X)
- Pu Chen (ORCID: https://orcid.org/0009-0007-5534-8986)
- Chi Yang (ORCID: https://orcid.org/0000-0002-3436-8554)
- Baoyue Cao (ORCID: https://orcid.org/0000-0003-4471-6337)
Institutions
- Rutgers, The State University of New Jersey (US)
- Baoji University of Arts and Sciences (CN)
- Shangluo University (CN)
- Xi'an Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-28
- DOI
- https://doi.org/10.1021/acs.joc.4c02132
- Citations
- 4
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shaanxi Province
- Science and Technology Innovation as a Whole Plan Projects of Shaanxi Province
- National College Students Innovation and Entrepreneurship Training Program