Simultaneous Construction of C−Se And C−S Bonds via the Visible‐Light‐Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO<sub>2</sub>

Chen, Hui; Ding, Rui; Tang, Hai‐Tao; Pan, Ying‐Ming; Xü, Yanli; Chen, Yanyan

doi:10.1002/asia.201901049

Cited by 31 publications

(25 citation statements)

References 49 publications

(19 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All these advantages have meant that in the last seven years there has been a significant increase in the number of works reporting the use of photochemistry in the seleno-functionalization of several classes of organic substrates [ 70 ]. For example, the carbon-selenium bond formation in heteroarene-like indoles [ 71 , 72 ], imidazo[1,2 a ]pyridines [ 73 , 74 ], coumarines [ 75 ], benzothiazoles [ 76 ] and pyridines [ 77 ]; selenylation of naphthols [ 78 ], terminal alkenes [ 79 , 80 ] and alkynes [ 81 , 82 ] and sp 3 carbons [ 83 , 84 ]; and selenocyclization reactions have been reported [ 85 , 86 ]. In these protocols, in general, the substrate, the selenylating reagent and the photocatalyst are stimulated by visible light irradiation via single electron transfer (SET) reactions.…”

Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

View full text Add to dashboard Cite

Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well as a powerful tool for modern organic synthesis, attracting the attention of the scientific community. This great success is mainly due to the breaking of paradigm demonstrated by innumerous works, that the selenium compounds were toxic and would have a potential impact on the environment. In this update review, we highlight the relevance of these compounds in several fields of research as well as the possibility to synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, as well as by the use of alternative energy sources, including mechanochemical, photochemistry, sonochemical and microwave irradiation.

show abstract

Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The synthesis of β ‐(seleno)‐vinyl sulfones was also carried out photochemically by Chen and co‐workers using alkynes 105 , diphenyl diselenide 50 , DABCO ⋅ (SO 2 ) 2 and blue LEDs with high selectivity for the E stereoisomer (Scheme 29). [54] The proposed mechanism involves a domino reaction, which begins with photochemical homolytic Se−Se bond cleavage of the diphenyl diselenide 50 leading to the phenylselenyl radical 119 . The addition of this radical to the terminal carbon on the alkyne produces the vinyl radical 124 , which traps SO 2 to afford the sulfonyl radical intermediate.…”

Section: Selenylation Of Other Multiple Bondsmentioning

confidence: 99%

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

Rafique

Rampon

Azeredo

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

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.

show abstract

“…Sun et al, reported a radical-initiated seleno difluoromethylation of alkenes promoted by copper salt. [179] Ogawa's group developed multicomponent cascade reactions of diselenide 4, alkyne 311 with: (i) alkene, [180][181][182][183][184][185][186] (ii) benzoyl peroxide (BPO), [187] and (iii) (Ph 2 P) 2 , [188] (iv) multicomponent cascade reaction of diselenides, alkynes, and sulfur dioxide by using a visible-light in which multiple CÀ Se and CÀ S bonds were constructed, [189] (v) palladium-catalyzed YÀ Y (Y=S, Se) bond addition to alkynes under solvent-free conditions (Scheme 100). [190] The synthesis of bis-selenide alkenes 319 and trisselenide alkenes 320 from alkynyl carboxylic acids 318 and diselenides 4 is shown in Scheme 101.…”

Section: Synthesis Of Bis-and Tris-selenide Alkenementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

show abstract

Simultaneous Construction of C−Se And C−S Bonds via the Visible‐Light‐Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO₂

Cited by 31 publications

References 49 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

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

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Contact Info

Product

Resources

About

Simultaneous Construction of C−Se And C−S Bonds via the Visible‐Light‐Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2

Cited by 31 publications

References 49 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

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

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Contact Info

Product

Resources

About

Simultaneous Construction of C−Se And C−S Bonds via the Visible‐Light‐Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO₂