Visible light-enabled synthesis of phosphorylated indolizine and pyridoindole derivatives via HAT-mediated radical cascade cyclization

Kunrong Shen; Chuan Feng; Yilei Liu; Dong Yi; Peng Lin; Huifang Li; Yimou Gong; Siping Wei; Qiang Fu; Zhijie Zhang

doi:10.1039/D3OB01675G

Visible light-enabled synthesis of phosphorylated indolizine and pyridoindole derivatives via HAT-mediated radical cascade cyclization†

Kunrong Shen,^a Chuan Feng,^a Yilei Liu,^a Dong Yi,

^a Peng Lin,^a Huifang Li,^a Yimou Gong,^a Siping Wei,

*^a Qiang Fu

*^a and Zhijie Zhang

*^ab

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* Corresponding authors

^a Green Pharmaceutical Technology Key Laboratory of Luzhou City, Central Nervous System Drug Key Laboratory of Sichuan Province, School of Pharmacy, Southwest Medical University, Luzhou, 646000, China
E-mail: zzj30@swmu.edu.cn, fuqiang@swmu.edu.cn, swei1225@swmu.edu.cn

^b State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou, China

Abstract

A visible light-enabled cascade cyclization strategy is disclosed with concomitant phosphorylation and heterocycle construction. It provides a novel and environmentally benign approach for accessing tetrahydroindolizine-containing phosphonates under metal-free conditions. Mechanistic studies revealed that phosphinoyl radicals were generated from H-phosphonates via a HAT process.

Organic & Biomolecular Chemistry

Visible light-enabled synthesis of phosphorylated indolizine and pyridoindole derivatives via HAT-mediated radical cascade cyclization†

Abstract

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Visible light-enabled synthesis of phosphorylated indolizine and pyridoindole derivatives via HAT-mediated radical cascade cyclization

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