Silver-Catalyzed Single-Carbon Insertion of Indoles with Acetophenone <i>N</i>-Triftosylhydrazones
Here, we report a silver carbene-enabled single-carbon insertion reaction of indoles via a one-pot, two-step sequence to deliver a dearomative quaternary center quinoline scaffold in a modular fashion. Specifically, we used <i>N</i>-triftosylhydrazones as masked donor-donor carbene precursors that facilitate the insertion of carbon atoms bearing various functional groups to the library of functionalized quinoline. Experimental and DFT evidence support the transient presence of a cyclopropane species and removal of protecting groups.
Authors
- Hongzhu Chen (ORCID: https://orcid.org/0000-0001-5338-0041)
- Xihe Bi (ORCID: https://orcid.org/0000-0002-6694-6742)
- Xiaolong Zhang (ORCID: https://orcid.org/0000-0002-5596-0776)
- Valentine G. Nenajdenko (ORCID: https://orcid.org/0000-0001-9162-5169)
- Menglin Liu (ORCID: https://orcid.org/0000-0001-9699-123X)
- Qingwen Zhu
- Hongru Zhang (ORCID: https://orcid.org/0000-0003-1959-3750)
- Linxuan Li (ORCID: https://orcid.org/0000-0001-9836-1442)
- Karunanidhi Murali
Institutions
- Northeast Normal University (CN)
- Lomonosov Moscow State University (RU)
- Nankai University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-15
- DOI
- https://doi.org/10.1021/acs.orglett.4c02633
- Citations
- 13
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 3.25
Funders
- National Natural Science Foundation of China