Metal-free difunctionalization of alkynes leading to alkenyl dithiocyanates and alkenyl diselenocyanates at room temperature

Lu, Linghui; Zhou, Si‐Jia; He, Wei-Bao; Wen, Xin; Chen, Ping; Yu, Xianyong; Xu, Xinhua; He, Wei‐Min

doi:10.1039/c8ob02368a

Cited by 97 publications

(32 citation statements)

References 90 publications

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“…[194][195] The synthesis of alkenyl diselenocyanate 324 has been developed via stereoselective difunctionalization of alkyne 323 with KSeCN at room temperature under mild and metal-free conditions by the simple use of PhI(OAc) 2 as the oxidant (Scheme 103). [196] The synthesis of Z-3-selenocyanatoacrylate 327 and analogues through green selenocyanation of activated alkyne 325 was successfully achieved by using lactic acid is shown in Scheme 104. [197] Also, the selective selenocyanation of activated alkynes 325 via an intermolecular H-bonding activation pathway has been achieved by using glycolic acid.…”

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

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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.

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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

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“…The expected alkenyl diselenocyanates 69 was obtained in good yield when alkynes 67 was treated with KSeCN [SeCN] source and PhI(OAc) 2 oxidant in H 2 O. 47 A possible mechanism for the difunctionalization of alkynes was proposed in Scheme 40. Firstly, in the presence of an oxidant oxone or PhI(OAc) 2 , NaSCN or KSeCN was converted into the SCN radical Q 0 or the SeCN radical S 0 .…”

Section: Other Cyanation Of Alkynesmentioning

confidence: 99%

Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes

Peng

Wang

et al. 2020

RSC Adv.

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“…In 2001, Moriarty disclosed the dithiocyanation of alkynes using in‐situ generated PhI(SCN) 2 with (dichloroiodo)benzene and Pb(SCN) 2 through an iodirenium ion intermediate (Scheme 1b) [5c] . In 2018, Xu and He, [6a] and Majee [6b] reported similar methodology of SCN⋅ radical addition reactions with MSCN (M=K, Na) and Oxone or sodium persulfate as the oxidant respectively (Scheme 1c). However, using heavy metals such as lead and excessive amount of oxidants sometime rise healthy and environmental concerns [7] .…”

Section: Introductionmentioning

confidence: 99%

Dithiocyanation of Alkynes with N‐Thiocyanato‐dibenzenesulfonimide and Ammonium Thiocyanate

et al. 2022

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Organic thiocyanates widely exist in natural products, and act as important precursors for organic synthesis. An efficient dithiocyanation of alkynes with N-thiocyanato-dibenzenesulfonimide (NTSI) as the SCN + cation and ammonium thiocyanate as the SCNanion sources has been developed. Highly active electrophilic reagent NTSI could react with various types of alkynes to build C(sp 2 )À SCN bond to provide a variety of dithiocyanato olefin compounds under simple and mild conditions. Trace amount of water is beneficial to the dissociation of ammonium thiocyanate, which makes the SCNanion easier to participate in the reaction. The protocol owns a broad substrates scope including terminal and internal, alkyl and aryl alkynes, excellent functional group tolerance and good regioselectivity.

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Metal-free difunctionalization of alkynes leading to alkenyl dithiocyanates and alkenyl diselenocyanates at room temperature

Abstract: A facile and efficient protocol for the construction of alkenyl dithiocyanates and alkenyl diselenocyanates has been developed via stereoselective difunctionalization of alkynes with NaSCN or KSeCN at room temperature.

Cited by 97 publications

References 90 publications

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

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

Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes

Dithiocyanation of Alkynes with N‐Thiocyanato‐dibenzenesulfonimide and Ammonium Thiocyanate

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