Visible-light-promoted radical cascade alkylation/cyclization: access to alkylated indolo/benzoimidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones

Yu, Wen-Qin; Xiong, Biquan; Zhong, Long-Jin

doi:10.1039/d2ob01732f

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob01732f

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Visible-light-promoted radical cascade alkylation/cyclization: access to alkylated indolo/benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

Wen-Qin Yu

Biquan Xiong

Long-Jin Zhong

Abstract: A new protocol is herein described for the direct generation of alkylated indolo/benzoimidazo[2,1-a]isoquinolin-6(5H)-one derivatives by using Hantzsch esters as alkylation radical precursors via photoredox/K2S2O8 system. This oxidative alkylation of active...

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Cited by 6 publications

References 121 publications

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Three‐Component Alkylsulfonylation of 1‐Acryloyl‐2‐Cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion

Zhong,

Shang,

Chen

et al. 2024

Eur J Org Chem

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A three‐component alkylsulfonylation/cyclization/ hydrolysis relay reaction of 1‐acryloyl‐2‐cyanoindoles with 4‐alkyl Hantzsch esters and Na2S2O5 to access a series of alkylsulfonyl pyrrolo[1,2‐a]indolediones derivatives involving in situ sulfur dioxide insertion is established. With this method, a variety of primary and secondary alkyl radicals can be used for trapping sulfur dioxide and in situ formed corresponding alkylsulfonyl radical intermediates, followed by alkyl sulfonyl radical addition, cyclization and hydrolysis. In addition, this reaction goes through once selective cleavage of σ carbon‐carbon bond and following successively formation of three new chemical bonds, in which cyano group acts as the dual roles, including the radical acceptor and carbonyl source.

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Three‐Component Alkylsulfonylation of 1‐Acryloyl‐2‐Cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion

Zhong,

Shang,

Chen

et al. 2024

Eur J Org Chem

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Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

Wang,

Zhou,

Zhang

et al. 2024

Green Synthesis and Catalysis

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Photoredox-catalyzed synthesis of α-alkylated unnatural amino acid derivatives with glyoxylimines and 4-alkyl-1,4-dihydropyridines

et al. 2023

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Visible-light-promoted radical cascade alkylation/cyclization: access to alkylated indolo/benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

Abstract: A new protocol is herein described for the direct generation of alkylated indolo/benzoimidazo[2,1-a]isoquinolin-6(5H)-one derivatives by using Hantzsch esters as alkylation radical precursors via photoredox/K2S2O8 system. This oxidative alkylation of active...

Cited by 6 publications

References 121 publications

Three‐Component Alkylsulfonylation of 1‐Acryloyl‐2‐Cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion

Three‐Component Alkylsulfonylation of 1‐Acryloyl‐2‐Cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion

Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

Photoredox-catalyzed synthesis of α-alkylated unnatural amino acid derivatives with glyoxylimines and 4-alkyl-1,4-dihydropyridines

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