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Three-Component Photocatalyzed Difunctionalization of Alkenes via Selective Remote 1,5-HAT of N-Alkoxyphthalimides
Tianle Huang1, Qing Liu1, Yafei Zhu1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, People's Republic of China.
Abstract:
Photocatalyzed difunctionalization of alkenes via radical-polar crossover (RPC) has been significantly advanced. N-Alkoxyphthalimides (NHPIs) have served as alkoxy radical precursors for alcohol synthesis. We report the first metal catalyst-free, three-component difunctionalization of alkenes employing NHPIs through selective remote 1,5-hydrogen atom transfer (HAT) and RPC. This protocol accommodates a broad substrate scope, affording products in moderate to good yields. Mechanistic studies (control reactions, radical/cation trapping, Stern-Volmer quenching, and cyclic voltammetry) elucidate the reaction pathway.
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