Radical-mediated photoredox hydroarylation with thiosulfonate

Wan, Xiaoyuan; Wang, Da‐Han; Huang, Huawen; Mao, Guojiang; Deng, Guo‐Jun

doi:10.1039/d2cc05948g

Cited by 22 publications

(4 citation statements)

References 48 publications

(18 reference statements)

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“…On the other hand, as one of the most attractive topics in organic chemistry, hydroarylation process has drawn interest of chemists in the past decades [18][19][20][21][22][23][24]. Recently, Pan and our group [25,26] independently reported a visible-light-induced hydrocyclization of unactivated alkenes which generated the polycyclic quinazolinones. (Figure 2a).…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides

Liu

Zhao

et al. 2023

Catalysts

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A novel metal-free photoredox-catalyzed cyclization reaction of N-aryl acrylamide is herein reported that provides synthetically valuable oxindole derivatives through the bis-mediation of H2O and aldehyde. In this work, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. The main characteristics of this reaction are environmentally friendly and high yields.

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Section: Introductionmentioning

confidence: 99%

Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides

Liu

Zhao

et al. 2023

Catalysts

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“…2c), on which we herein report in line with our on-going program on sustainable photochemistry. 13 Notably, 2,3-fused N -acryloyl indoles such as tetrahydrocarbazole compounds are used to expectedly deliver underrepresented tetracyclic products, which could significantly enrich the 3D chemical space of indole-based molecules.…”

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confidence: 99%

Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles

Liu,

Ji,

Duan

et al. 2024

Chem. Commun.

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“…Nevertheless, the site-selectivity control at the same catalyst by switching the nitrogen substituents has not been well-documented. − Besides, cyclization of unprotected N -H- N -arylacrylamides via visible light photocatalysis has not been reported.…”

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confidence: 99%

Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

et al. 2023

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CBZ6, a redox-neutral non-donor–acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant or oxidant is involved. This process provides a concise and environmentally sustainable access to a series of oxindoles and dihydroquinolinones.

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Radical-mediated photoredox hydroarylation with thiosulfonate

Abstract: Herein, we report a novel visible light-induced photocatalytic system that enables intramolecular hydroarylation of unactivated alkenes. Thiosulfonate compounds were found to be the key radical precursor that mediates the Minisci-type...

Cited by 22 publications

References 48 publications

Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides

Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides

Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles

Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

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