Electrochemical reaction of indole-tethered alkynes enabling stereoselective synthesis of iodovinyl spiroindolenine-cyclopentanes
A novel electrochemical iodination/spirocyclization reaction of 3-alkynyl indoles with <i>n</i>-Bu<sub>4</sub>NI as coupling partner and electrolyte is developed, which affords iodovinyl spiroindolenine-cyclopentanes as products in excellent yields and high <i>E</i>-stereoselectivities. This reaction tolerates a wide range of 3-alkynyl indoles and iodide sources, which represents the first example of the electrosynthesis of spiroindolenine-cycloalkanes.
Authors
- Ata Makarem (ORCID: https://orcid.org/0000-0003-1291-4312)
- Xinrui Zhou (ORCID: https://orcid.org/0000-0002-7104-6749)
- Jingrui He
- Vadim A. Soloshonok (ORCID: https://orcid.org/0000-0003-0681-4526)
- Ramin Javahershenas (ORCID: https://orcid.org/0000-0001-5771-7203)
- Haibo Mei (ORCID: https://orcid.org/0000-0002-2857-1935)
- Jianlin Han (ORCID: https://orcid.org/0000-0002-3817-0764)
Institutions
- Ikerbasque (ES)
- Universität Hamburg (DE)
- Nanjing Forestry University (CN)
- University of the Basque Country (ES)
- Urmia University (IR)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc01342a
- Citations
- 9
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 8.42