Visible-light-induced metal and reagent-free oxidative coupling of <i>sp</i><sup>2</sup> C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles

Rathore, Vandana; Kumar, Sangit

doi:10.1039/c9gc00007k

Cited by 113 publications

(48 citation statements)

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“…In recent years, several photochemical C-Se bond formation reactions have been reported [ 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. The use of photocatalysts is one of the effective methods to achieve this type of transformation under visible light irradiation [ 34 , 35 ].…”

Section: Resultsmentioning

confidence: 99%

“…The use of photocatalysts is one of the effective methods to achieve this type of transformation under visible light irradiation [ 34 , 35 ]. Photocatalyst-free C-Se bond formation reactions under UVA [ 38 ] or visible light [ 36 , 37 , 39 ] irradiation have also been reported, but an oxidant (O 2 ) or a base is often needed. The present reaction provides a new and simple photochemical C-Se bond formation reaction without a photocatalyst or a base.…”

Section: Resultsmentioning

confidence: 99%

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Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

et al. 2021

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In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy•). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

et al. 2021

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“…The indolyl radical 28 a on reaction with chalcogenide 26 , forms arylchalcogenyl indole cation 30 and organochalcogenyl radical 29 . Hydrogen abstraction of the carbon 3 by the anion radical of O 2 .− then leads to the formation of the desired 3‐chalcogenylindoles 27 [21] …”

Section: Selenylation Of (Hetero)arenesmentioning

confidence: 99%

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

Rafique

Rampon

Azeredo

et al. 2021

The Chemical Record

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Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well as in modern organic synthesis, attracting considerable attention from the scientific community. Therefore, the construction of the C−Se bond via facile, efficient and sustainable strategies to access complex scaffolds from simple substrates are an appealing and hot topic. Visible light can be regarded as an alternative source of energy and is associated with environmentally‐friendly processes. Recently, the use of visible‐light mediated seleno‐functionalization has emerged as an ideal and powerful route to obtain high‐value selenylated products, with diminished cost and waste. This approach, involving photo‐excited substrates/catalyst and single‐electron transfer (SET) between substrates in the presence of visible light has been successfully used in the versatile and direct insertion of organoselenium moieties in activated and unactivated C(sp3)−H, C(sp2)−H, C(sp)−H bonds as well as C−heteroatom bonds. In most cases, ease of operation and accessibility of the light source (LEDs or commercial CFL bulbs) makes this approach more attractive and sustainable than the traditional strategies.

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“…Kumar and co‐workers also developed a photocatalyst‐/base‐/metal‐free visible light‐induced protocol for the synthesis of 3‐organochalcogenyl indoles through the construction of C‐chalcogen (S, Se, Te) bond using O 2 as an oxidant (Scheme 117). [180] Various diaryl selenides/tellurides/sulfides, ammonium thiocyanate, and the heterocyclic unsymmetrical chalcogenides with indoles are converted to the corresponding products in excellent yield. The plausible mechanism is shown in scheme 117.…”

Section: Photo‐catalyzed/promoted Functionalization Of Indole Derivatmentioning

confidence: 99%

“…Kumar and co-workers also developed a photocatalyst-/base-/metal-free visible light-induced protocol for the synthesis of 3-organochalcogenyl indoles through the construction of C-chalcogen (S, Se, Te) bond using O 2 as an oxidant (Scheme 117). [180] Various diaryl selenides/tellurides/sulfides, ammonium thiocya-…”

Section: O 2 Oxidation Photocatalysismentioning

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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Visible-light-induced metal and reagent-free oxidative coupling of sp² C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles

Abstract: Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C–H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone.

Cited by 113 publications

References 82 publications

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

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

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Visible-light-induced metal and reagent-free oxidative coupling of sp2 C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles

Abstract: Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C–H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone.

Cited by 113 publications

References 82 publications

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

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

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Product

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Visible-light-induced metal and reagent-free oxidative coupling of sp² C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles