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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible-Light-Driven Photocatalytic Synthesis of Polysubstituted Pyrrolidines via Desulfurative Tandem Cyclization of
Hongda Xia1, Hengming Yang1, Jiangna Yue1
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-enynes with thiols was successfully developed. This method provides efficient access to a wide range of five-membered heterocyclic compounds in good to excellent yields with high regioselectivity through a desulfurative/cyclization/HAT process. The versatility of this reaction is demonstrated by its compatibility with a variety of N-tethered 1,6-enynes, encompassing diverse electronic and steric properties. Notably, the cascade reaction demonstrates remarkable operational simplicity, high bond-forming efficiency, and potential scalability, as exemplified by its successful implementation in gram-scale synthesis, which is expected to have potential applications in organic synthesis.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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