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Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols

Haiqian Zhu, Hanliang Zheng, Junhua Zhang, Jian Feng, Lichun Kong, Fang Zhang, Xiao‐Song Xue, Gangguo Zhu

2021Chemical Science29 citationsDOIOpen Access PDF

Abstract

-dimethylacetamide-assisted 1,2-hydrogen transfer of alkoxy radicals is responsible for the cyclopentenone formation, whereas a C-C cleavage accounts for the selective production of dihydropyranols in acetonitrile and water at 50 °C. Given the simple and mild reaction conditions, excellent functional group compatibility, forming up to four chemical bonds, and tunable selectivity, it may find wide applications in synthetic chemistry.

Topics & Concepts

PhotocatalysisSolventChemistryAldehydeCombinatorial chemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols | Litcius