Synthesis of δ-phosphorothiolated alcohols by photoredox/copper catalyzed remote C(sp3)–H phosphorothiolation of N-alkoxypyridinium salts

文献情報

出版日 2021-10-02

DOI 10.1039/D1QO01178B

インパクトファクター 5.281

著者

Zhipeng Zheng, Shanshan Shi, Qianru Ma, Yufei Yang, Yan Liu, Guo Tang

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要旨

Incorporation of the (RO)2P(O)S group through unreactive C(sp3)–H phosphorothiolation remains a challenging area of research. Under mild photoredox/copper catalysis, the reaction of readily available (EtO)2P(O)SH with N-alkoxypyridinium salts afforded δ-phosphorothiolated alcohols in good yields. The δ-C(sp3)-phosphorothiolation reaction went through a cascade process involving photo-promoted alkoxy radical generation, 1,5-hydrogen atom transfer, and Cu-catalyzed cross-coupling of the δ-C(sp3)-centered radical with (EtO)2P(O)SH. In addition, this photoredox/copper system also enabled O-radical ring-closure and phosphorothiolation from N-alkenyloxypyridinium salts to form β-phosphorothio tethered tetrahydrofurans.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of δ-phosphorothiolated alcohols by photoredox/copper catalyzed remote C(sp3)–H phosphorothiolation of N-alkoxypyridinium salts

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