Synthesis of 3-Chloro-benzo[<i>b</i>]selenophenes from Diphenylpropynones via PhICl<sub>2</sub>/KSeCN-Mediated Successive Bond Formation
The reaction of diphenylpropynones with PhICl<sub>2</sub>/KSeCN in DMSO was found to deliver 3-chloro-benzo[<i>b</i>]selenophenes via an exclusive intramolecular cyclization encompassing oxidative C-Se/C-Cl bond formation. The electrophilic Cl-SeCN, generated in situ from the reaction of PhICl<sub>2</sub> and KSeCN, was postulated to be crucial for annulation to occur.
Authors
- Dongxue Yin
- Dan Xiao (ORCID: https://orcid.org/0000-0003-2484-1405)
- Yunfei Du (ORCID: https://orcid.org/0000-0002-0213-2854)
- Q. Kevin Fang
- Kaiyue Yang
- Zhijian Wang (ORCID: https://orcid.org/0000-0003-2929-8376)
- Yingjie Gao (ORCID: https://orcid.org/0000-0003-4397-0990)
- Xiaotong Wang (ORCID: https://orcid.org/0000-0003-3998-3350)
Institutions
- Tianjin University (CN)
- Tianjin Institute of Pharmaceutical Research (China) (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-22
- DOI
- https://doi.org/10.1021/acs.joc.5c01764
- Primary Topic
- Synthesis and Biological Evaluation
- Type
- article
- Field-Weighted Citation Impact
- 0.00