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

Emma Campbell, Andrea Taladriz-Sender, Olivia I. Paisley, Alan R. Kennedy, Jacob T. Bush, Glenn A. Burley

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)
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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.

Original languageEnglish
Pages (from-to)4603-4616
Number of pages14
JournalJournal of Organic Chemistry
Volume87
Issue number7
Early online date18 Mar 2022
DOIs
Publication statusPublished - 1 Apr 2022

Keywords

  • carbazoles
  • Buchwald–Hartwig amination
  • anti-cancer agents

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