An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles
Abstract A simple, expedient continuously scalable flow chemistry synthesis of a range of 1,4‐dimethylcarbazoles from substituted indoles and 2,5‐hexanedione in the presence of K‐10 (montmorillonite clay) is reported. Optimization of the flow conditions led to the development of an in‐house K‐10/sand Omnifit TM catalyst column that at 140 °C and 0.4 mL.min −1 afforded >90% conversion of the selected indole to the desired 1,4‐carbazole. This equates to a ca 80 mg.h −1 production rate. The reaction was tolerant of electron donating indoles but not electron withdrawing indoles.
Authors
- Adam McCluskey (ORCID: https://orcid.org/0000-0001-7125-863X)
- Jennifer R. Baker (ORCID: https://orcid.org/0000-0002-9560-301X)
- Cecilia C. Russell (ORCID: https://orcid.org/0000-0001-8401-5856)
- Michael C. Hamilton (ORCID: https://orcid.org/0000-0002-8635-6790)
- Fiona M. Deane
- Louis E Matheson
Institutions
- University of Newcastle Australia (AU)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2025-03-28
- DOI
- https://doi.org/10.1002/slct.202500249
- Primary Topic
- Synthesis and Biological Evaluation
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Ramaciotti Foundations
- Australian Cancer Research Foundation
- Australian Research Council