Photocatalytic direct C–S bond formation: facile access to 3-sulfenylindoles via metal-free C-3 sulfenylation of indoles with thiophenols

Guo, Wei; Tan, Wen; Zhao, Mingming; Tao, Kailiang; Zheng, Lvyin; Wu, Yongquan; Chen, Deliang; Fan, Xiaolin

doi:10.1039/c7ra08086g

Cited by 67 publications

(32 citation statements)

References 39 publications

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“…Miyake et al reported the visible light-promoted cross-coupling reaction between aryl halides and arylthiols via an intermolecular charge transfer using Cs 2 CO 3 as base [ 41 ]. Two recent reports showed the synthesis of C-3 sulfenylated indoles and 3-sulfenylimidazopyridine via C–H functionalization using Rose Bengal as photocatalyst [ 42 – 43 ]. In general, the arylation reactions use the reductive cycle of the photocatalyst and for this, electron poor arenes are required.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

Das

Maity

Malcherek

et al. 2018

Beilstein J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

Das

Maity

Malcherek

et al. 2018

Beilstein J. Org. Chem.

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“…Our group successfully completed an attractive strategy for direct assembly of 3‐sulfenylindoles via photocatalytic direct C‐3 sulfenylation of indoles with thiophenols under mild conditions (Scheme 94). [10b] At room temperature, various indoles and thiophenols can be effectively converted into structurally diverse products using Rose Bengal as a photocatalyst and air as an oxidant. We proposed a plausible mechanism.…”

Section: Photo‐catalyzed/promoted Functionalization Of Indole Derivatmentioning

confidence: 99%

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

2020

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The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality and economy. Recently, photoredox catalysis has shown great application values in organic transformations because of its advantages of environmentally friendly and abundant resources. Indoles and their derivatives (indolines, oxindoles and isatins) are the core skeletons of some important organic compounds and widely‐present in various natural products and pharmaceuticals with different biological activities. Therefore, the research on the synthesis and modification of indoles is particularly important for chemists and pharmacologists. This review summarizes the effects of photocatalysis on indole synthesis and modification in recent decades. These transformations are accomplished by using metal photocatalysts (i. e., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO2, etc.) or non‐metallic photocatalysts (i. e., Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), or without the need of photocatalysts. The detailed mechanisms of these photo‐catalyzed/promoted organic reactions are also highlighted deeply. And we hope this review will be helpful to researchers interested in this promising field of photocatalyzed transformations.

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“…[98] In 2017, Chen and Fan realized an efficient C3 sulfenylation of indoles with thiophenols through visible light-induced photocatalysis using Rose Bengal as the photosensitizer (Scheme 38). [99] On the basis of experimental results, a reaction mechanism involving singlet oxygen generated by energy transfer from excited rose bengal was proposed. Although the yields of 3-sulfenylation products are generally moderate, the present synthetic protocol with low catalyst loading provides a really facile and mild entry to the target transformation.…”

Section: Indole Sulfenylationmentioning

confidence: 99%

Aerobic Oxidative Functionalization of Indoles

et al. 2020

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The synthetic methodology for direct indole functionalizations is of great significance in indole chemistry and has been intensively investigated in the last few decades. From the perspective of green chemistry, oxygen is the best choice as the terminal oxidant in molecular synthesis. Hence, aerobic oxidative functionalization of indoles became a hot research topic in the last decade. Numerous efficient protocols in this field have been discovered that enable facile and efficient transformations of indoles to related valuable compounds, which are summarized and discussed in detail in this review.

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Photocatalytic direct C–S bond formation: facile access to 3-sulfenylindoles via metal-free C-3 sulfenylation of indoles with thiophenols

Abstract: An efficient and convenient photocatalytic direct C-3 sulfenylation of indoles with thiophenols has been developed for the construction of 3-sulfenylations.

Cited by 67 publications

References 39 publications

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

Aerobic Oxidative Functionalization of Indoles

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