Nucleophilic disulfurating reagents for unsymmetrical disulfides construction via copper-catalyzed oxidative cross coupling

Dai, Zhihong; Xiao, Xiao; Jiang, Xuefeng

doi:10.1016/j.tet.2017.05.010

Cited by 49 publications

(11 citation statements)

References 71 publications

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“…Jiang and coworkers reported a disulfuration through copper‐catalyzed oxidative Hiyama ‐type cross‐coupling for the synthesis of asymmetrical disulfide ( Scheme 8). [38] The pH of the medium plays an important role in the in‐situ formation of a disulfur anion through the alcoholysis of disulfane reagent, and the highest yield was obtained when TsOH⋅H 2 O was used as pH value conditioner. Arylsilane bearing amide‐ and halogen‐substituted, thiophene and alkylsilane were proceed smoothly and gave the corresponding products in high yields.…”

Section: Synthesis Of Unsymmetrical Organic Disulfidesmentioning

confidence: 99%

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Ong

Titinchi

Juan

et al. 2021

Helvetica Chimica Acta

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Organic unsymmetrical disulfides have been extensively applied in various academic and industrial fields including intermediates in organic synthesis, agriculture, and food science, natural materials, biochemistry, pharmaceutical and medicine chemistry, polymers, material engineering, etc. They play a crucial role in the fabrication of various biological active sulfur heterocycles. Due to broad and extensive applications, many methods have been developed for the synthesis of unsymmetrical S−S and efforts have been made to improve some issues such as cost, energy efficiency, green chemistry, avoid or minimizing waste generation. Several outstanding review articles have been previously published highlighting the advances of S−S bond formation, in general, using various reagents under different conditions in the absence or presence of oxidants/catalysts. In 2020, a review paper was published by our group focusing on recent developments since 2014 in the synthesis of organic symmetrical disulfides. However, investigations on new catalytic methods are being regularly reported and new types of unsymmetrical disulfides are synthesized. The present overview has attempted to systematically summarize recent advances in the process of unsymmetrical S−S bond formation with a major focus since 2010, highlighting mechanistic considerations, substrate scope, advantages, and limitations. The patents are not studied in this overview.

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Section: Synthesis Of Unsymmetrical Organic Disulfidesmentioning

confidence: 99%

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Ong

Titinchi

Juan

et al. 2021

Helvetica Chimica Acta

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“…Thus, it can recognize the non‐ionic nitroolefin 115 [66d–h] through the H‐bond interaction to control the enantioselectivity. The catalyst of 2,6‐lutidine as Brønsted base can deprotonate the acidic nucleophile of thiol 116 , and then leading to realizing the asymmetric sulfa‐Michael addition and affording the desired sufide 117 [66i–t] . The diverse derivatization finally transfers the sulfide 117 to the bioactive molecules of taurine derivative 118 and 4‐monosubstituted β ‐sultam 119 .…”

Section: Asymmetric Reactions Catalyzed By Multi‐organocatalystsmentioning

confidence: 99%

Recent Advances in Asymmetric Organomulticatalysis

Xiao

Shao

et al. 2020

Adv Synth Catal

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Asymmetric multi‐catalysis, designed to mimic catalytic processes in nature, is a powerful instrument to fulfil fascinating transformations. As a result, this area of research has attracted considerable interests within chemistry communities. Although there are numerous reviews involving multi‐catalysis, reviews describing asymmetric organomulticatalysis remain rare. Taking into consideration that organocatalysts possess the superiorities of effortless availability, inexpensiveness, hypotoxicity, facile handling and hyposensitivity to moisture and oxygen, they have definite advantage in their own distinct modes of activation when utilized in multi‐catalytic reactions. Organomulticatalysis refers to the synthetic strategies of modular combination of organo‐catalyzed reactions into one synthetic operation with minimum workup or change in conditions. It is apparent that a variety reports utilizing the concept of enantioselective organomulticatalysis have substantially surfaced in the past few years. Hence, it is indispensable to succinctly present all such reports by means of disclosing the mechanistic analysis, as well as the challenges and issues associated in the development of the asymmetric catalytic system. Additionally, this review will introduce some of the unsettled conundrums and possible innovations in this field.

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“…The most common synthesis of disulfide functionality is based on the nucleophilic substitution reaction of a sulfenyl derivative with a thiol or thiol derivative. The most frequently utilized electrophilic sulfenyl derivatives are: sulfenyl chlorides [ 23 , 24 ], S -alkylsulfanylisothioureas [ 25 , 26 ], S -alkyl thiosulfates and S -aryl thiosulfates (Bunte salts) [ 27 ], benzotriazolyl sulfanes [ 28 , 29 ], benzothiazol-2-yl disulfides [ 30 ], (alkylsulfanyl)dialkylsulfonium salts [ 31 , 32 ], dithioperoxyesters [ 33 ], 2-pyridyl disulfides and derivatives [ 34 , 35 ], sulfonamides [ 36 ], N -alkyltetrazolyl disulfides [ 37 ], sulfenyl thiocyanates [ 38 ], sulfenyldimesylamines [ 39 ], thiolsulfinates [ 40 ] and thiosulfonates [ 41 , 42 , 43 ], 4-nitroarenesulfenanilides [ 44 ], thionitrites [ 45 ], thioimides [ 46 ], sulfenyl sulfanylsulfinamidines [ 47 , 48 , 49 ], and thiophosphonium salts [ 50 ]. The disulfides can also be efficiently obtained by the reaction of a thiol with a sulfinylbenzimidazole [ 51 ], a disulfide exchange reaction promoted by rhodium catalyst [ 52 , 53 ], an electrochemical method [ 54 ], using tetrathiomolybdate in the presence of a symmetrical disulfide to promote a ring opening of an aziridine [ 55 , 56 ], or the application of diethyl azodicarboxylate (DEAD) [ 57 ] or a solid support [ 58 ] to promote a sequential coupling of two different thiols.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

et al. 2021

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The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of S-vinyl phosphorodithioate with thiotosylates or S-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[b][1,4]thiazine derivatives.

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Nucleophilic disulfurating reagents for unsymmetrical disulfides construction via copper-catalyzed oxidative cross coupling

Cited by 49 publications

References 71 publications

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides

Recent Advances in Asymmetric Organomulticatalysis

Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

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