A Chemo- and Regioselective Tandem [3 + 2]Heteroannulation Strategy for Carbazole Synthesis: Combining Two Mechanistically Distinct Bond-Forming Processes.

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.

• Authors: Emma Campbell, Andrea Taladriz-Sender, Olivia I Paisley, Alan R Kennedy, Jacob T Bush, Glenn A Burley
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 87 Issue 7 Pg. 4603-4616 (04 01 2022) ISSN: 1520-6904 [Electronic] United States
• PMID: 35302774 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Carbazoles
• Palladium

Topics

• Amination
• Carbazoles
• Catalysis
• Palladium