Photoinduced Cyclizations of <i>o</i>-Diisocyanoarenes with Organic Diselenides and Thiols that Afford Chalcogenated Quinoxalines

Tran, Cong Chi; Kawaguchi, Shin‐ichi; Sato, Fumiya; Nomoto, Akihiro; Ogawa, Akira

doi:10.1021/acs.joc.0c00647

Cited by 37 publications

(38 citation statements)

References 43 publications

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“…In this context, the synthesis of bis ‐selenylquinoxalines 162 from o ‐diisocyanoarenes and diaryl or dialkyl diselenides, in moderate to good yields, was reported by Tran and coworkers (Scheme 39). [65] …”

Section: Cyclizationmentioning

confidence: 99%

“…In the second proposition (path B ), the R 2 Se radical species attacks the isocyanide group to form the imidoyl radical intermediate 163 followed by intramolecular addition to the vicinal isocyanide group. Finally, intermediate 164 , react with another equivalent of diorganoyl diselenide 11 affording the bis ‐selenylquinoxalines 162 [65] …”

Section: Cyclizationmentioning

confidence: 99%

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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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Section: Cyclizationmentioning

confidence: 99%

Section: Cyclizationmentioning

confidence: 99%

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

Rafique

Rampon

Azeredo

et al. 2021

The Chemical Record

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“…The radical addition reactions of halogens and organic disulfides have been reported to occur under photoirradiation, but their synthetic applications are limited. To clarify the universality of the photoinduced radical reaction of heteroatom compounds as a method for generating carbon-heteroatom bonds, we previously investigated a series of radical addition reactions to the carbon-carbon unsaturated bonds, of group 16 (e.g., diselenides and ditellurides) [32][33][34][35][36], group 15 (e.g., diphosphines) [37][38][39][40][41][42], and group 13 (e.g., diboranes) compounds [43,44]. We then combined these reactions with disulfides and fluorinated iodoalkanes and successfully formed a variety of carbon-heteroatom bonds [45][46][47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization

et al. 2022

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The addition of interelement compounds with heteroatom-heteroatom single bonds to carbon-carbon unsaturated bonds under light irradiation is believed to be an atomically efficient method to procure materials with carbon-heteroatom bonds. In this study, we achieved the photoinduced bisphosphination of alkynes using the phosphorus interelement compound, tetraphenyldiphosphine monosulfide (1), to stereoselectively obtain the corresponding (E)-vic-1,2-bisphosphinoalkenes, which are important transition-metal ligands. The bisphosphination reaction was performed by mixing 1 and various alkynes and then exposing the mixture to light irradiation. Optimization of the conditions for the bisphosphination reaction resulted in a wide substrate range and excellent trans-selectivity. Moreover, the completely regioselective introduction of pentavalent and trivalent phosphorus groups to the terminal and internal positions of the alkynes, respectively, was achieved. We also found that the novel double-bond isomerization reaction of the synthesized bisphosphinated products occurred with a catalytic amount of a base under mild conditions. Our method for the photoinduced bisphosphination of carbon-carbon unsaturated compounds may have strong implications for both organic synthesis and organometallic and catalyst chemistry.

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“…Therefore, the development of innovative molecular transformation methods based on the elucidation of unexplored elemental properties is essential. By focusing on the radical reaction properties of organochalcogen compounds, we successfully developed a series of new addition reactions based on radical mechanisms [ 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. These reactions can be induced by light irradiation and exhibit high functional group selectivity, which is a characteristic of radical reactions.…”

Section: Introductionmentioning

confidence: 99%

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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Photoinduced Cyclizations of o-Diisocyanoarenes with Organic Diselenides and Thiols that Afford Chalcogenated Quinoxalines

Cited by 37 publications

References 43 publications

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

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

Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

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