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A Chemo- and Regioselective Tandem [3 + 2]Heteroannulation Strategy for Carbazole Synthesis: Combining Two Mechanistically Distinct Bond-Forming Processes.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Apr 01; Vol. 87 (7), pp. 4603-4616. Date of Electronic Publication: 2022 Mar 18. - Publication Year :
- 2022
-
Abstract
- A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.
- Subjects :
- Amination
Catalysis
Carbazoles
Palladium
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35302774
- Full Text :
- https://doi.org/10.1021/acs.joc.1c02943