A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis : combining two mechanistically distinct bond-forming processes

Campbell, Emma and Taladriz-Sender, Andrea and Paisley, Olivia I. and Kennedy, Alan R. and Bush, Jacob T. and Burley, Glenn A. (2022) A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis : combining two mechanistically distinct bond-forming processes. Journal of Organic Chemistry, 87 (7). pp. 4603-4616. ISSN 0022-3263 (https://doi.org/10.1021/acs.joc.1c02943)

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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.

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