I<sub>2</sub>-Induced Metal-Free C(sp<sup>2</sup>)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1<i>H</i>-indoles
The I<sub>2</sub>-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment with K<sub>2</sub>CO<sub>3</sub> provided (benzofuran-3-yl)-1<i>H</i>-indoles in good to excellent yields with high regioselectivity. This one-pot and two-step strategy proved to be suitable for a wide range of substrates except for aliphatic alkynyl alcohols as well as the indoles bearing <i>N</i>-protected groups such as the Ts group possessing strong electron-withdrawing feature. The reaction procedure involved a cross-coupling and the construction of a benzofuran framework via 5-<i>exo-dig</i> cyclization.
Authors
- Yang Zhu
- Guisheng Deng (ORCID: https://orcid.org/0000-0002-6132-5648)
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Hunan Normal University (CN)
- Laboratoire de Synthèse Organique (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-03
- DOI
- https://doi.org/10.1021/acs.joc.4c03109
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Science and Technology Program of Hunan Province
- Construct Program of the Key Discipline in Hunan Province