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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible-Light Photoredox-Catalyzed Tandem Cyclization of 1,6-Dienes/Enynes with Thiols: Access to Sulfur-Substituted
Hongda Xia1, Chongchong Ma1, Hengming Yang1
1Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Abstract:
A metal-free, visible-light photoredox-catalyzed tandem cyclization of 1,6-dienes/enynes with thiols was successfully developed. This method provides efficient access to diverse five- and six-membered sulfur-substituted heterocyclic compounds─including tetrahydrofurans, pyrrolidines, tetrahydropyrans, and piperidins in good to excellent yields with high regio- and stereoselectivity. The broad reaction scope is demonstrated with a wide range of 1,6-dienes/enynes and thiols. This cascade exhibits high bond-forming efficiency, exceptional operational simplicity, and high potential scalability. Furthermore, the resulting heterocyclic sulfides can be readily oxidized to furnish the corresponding sulfoxides, thereby enhancing their synthetic versatility.
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