C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of <i>N</i>-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides
A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with <i>N</i>-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the <i>para</i> position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.
Authors
- Michael G. Gardiner (ORCID: https://orcid.org/0000-0001-6373-4253)
- Christopher Richardson (ORCID: https://orcid.org/0000-0002-5804-6322)
- Steven M. Wales (ORCID: https://orcid.org/0000-0003-0637-4225)
- Lillian A. de Ceuninck van Capelle (ORCID: https://orcid.org/0000-0003-4966-1806)
- Christopher J. T. Hyland (ORCID: https://orcid.org/0000-0002-9963-5924)
- Rasool Babaahmadi (ORCID: https://orcid.org/0000-0002-2580-6217)
- John H. Ryan (ORCID: https://orcid.org/0000-0003-2192-5099)
- James M. MacDonald
- Kimia Rahmannia
Institutions
- Australian National University (AU)
- University of Wollongong (AU)
- CSIRO Manufacturing (AU)
- Cardiff University (GB)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-18
- DOI
- https://doi.org/10.1021/acs.joc.4c02231
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Commonwealth Scientific and Industrial Research Organisation
- University of Wollongong
- Australian Research Council