Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents
Jiaqiong Sun,
Yunliang Guo,
Jiuli Xia,
Guangfan Zheng,
Qian Zhang
Affiliations
Jiaqiong Sun
School of Environment, Northeast Normal University, Changchun 130117, China
Yunliang Guo
School of Environment, Northeast Normal University, Changchun 130117, China
Jiuli Xia
Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province, Department of Chemistry, Northeast Normal University, Changchun 130024, China
Guangfan Zheng
Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province, Department of Chemistry, Northeast Normal University, Changchun 130024, China
Qian Zhang
Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province, Department of Chemistry, Northeast Normal University, Changchun 130024, China
β-halogenated enol esters and ethers are versatile building blocks in organic synthesis, which has attracted increasing attention. In this study, we report the facile trans-oxyiodination and oxychlorination of alkynes, leading to the direct construction of versatile halogenated enol esters and ethers. This transformation features an easy operation, optimal atomic economy, a strong functional group tolerance, broad substrate scope, and excellent trans-selectivity. Employing highly electrophilic bifunctional N–X (halogen) reagents was the key to achieving broad reaction generality. To our knowledge, this transformation represents the first oxyhalogenation system employing N–X (halogen) reagents as both oxylation and halogenation sources.
