Recent Catalytic Advances in the Synthesis of Organic Symmetric Disulfides

Ling, Ong Chiu; Khaligh, Nader Ghaffari; Juan, Joon Ching

doi:10.2174/1385272824666200221111120

Cited by 17 publications

(3 citation statements)

References 99 publications

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“…Compared with organic SB, common organic bases exhibited longer reaction time and/or lower yield of 2a (Table 1, entries [7][8][9][10][11][12][13][14][15][16][17]. The main reason why the catalytic effect of organic SB is better than that of common base is that the pK BH + value of organic SB is greater than that of ordinary base, There is no doubt that the strong alkalinity of organic SB is much favorable for the deprotonation of RSH because the pKa of 1a is about 10.7 (in water) [32].…”

Section: Comparison Of Catalytic Performance Of Various Organic Basesmentioning

confidence: 99%

“…Synthetic disul des have been widely used in various organic conversion of synthetic intermediates [3], fragrances [4], pesticides [5], industrial polymers [6], lithium ion batteries and other elds [7]. Since mercaptan is a commercially available and readily synthesized material, oxidative coupling of mercaptan is considered to be the optimal and most straight forward route for preparing disul de compounds [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

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Organic superbase-catalyzed oxidation of alkanethiols to dialkyl disulfides by elemental sulfur

Zhang

Wang

et al. 2023

Res Chem Intermed

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Under atmospheric pressure and solvent-free conditions, organic superbase (SB) catalyzed the oxidation of alkanethiols (RSH) to dialkyl disul de (R 2 S 2 ) by using sulfur as oxidant was investigated. The results showed that amidines (DBU, DBN) and guanidines (BTMG, MTBD, TMG) exhibited signi cantly higher catalytic activity than common organic bases. Under the condition of 3.0 molar ratio of RSH/S (50 mol% excess of RSH), 99~100% yield of (n-C 8 H 17 ) 2 S 2 could be obtained with 0.1 mol% SB and more than 95% yield of (n-C 8 H 17 ) 2 S 2 could be also obtained even if with 0.001 mol% SB. The yield of target product R 2 S 2 (R = alkyl, phenyl) was still obtained above 90% when the molar ratio of RSH/S was 2.1 (5 mol% excess of RSH). R 2 S 3 was the only by-product, and no R 2 S 4 was generated. The deprotonation ability of SB to RSH is signi cantly higher than that of common organic bases, and RS − is the key active species in the catalytic reaction. This synthetic method has the advantages of operational simplicity, inexpensive, and the applicability to 20-30 g scale synthesis strengthen its potential applications for preparing disul de at an industrial scale.

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Section: Comparison Of Catalytic Performance Of Various Organic Basesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Organic superbase-catalyzed oxidation of alkanethiols to dialkyl disulfides by elemental sulfur

Zhang

Wang

et al. 2023

Res Chem Intermed

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“…Traditionally, during the chemical synthesis of disulfides, stoichiometric strong oxidizing agents such as iodine/bromine [22], hydrogen peroxide [23], ammonium peroxydisulfate [24], and Cu(NO 3 ) 2 •H 2 O [25] are employed. Nevertheless, the employment of stoichiometric oxidizing agents always results in environmental concerns, along with the formation of over-oxidized by-products of thiol, including thiosulfinate, thiosulfonate, and sulfonic acids [26]. Given these issues, the catalytic oxidation of thiols using environmentally benign terminal oxidants like molecular oxygen or air has attracted increasing interest.…”

Section: Introductionmentioning

confidence: 99%

Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation

Chen,

Li,

et al. 2024

Organics

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Polyether amines are versatile compounds characterized by a flexible structure, consisting of polyoxypropylene and polyoxyethylene as the backbone, with amine groups at each end. They have widespread applications in various industrial processes and daily life. Despite their versatility, the utilization of polyether amines as base catalysts is rare. In this study, one kind of three-arm polyether amine 1 was employed as an environmentally friendly, cost-effective catalyst for the aerobic oxidation of thiophenols, leading to the synthesis of disulfides. The oxidative coupling of thiols serves as a fundamental pathway for the production of disulfides, which are vital in both chemical and biological processes. In contrast to known methods for thiol oxidation, this polyether amine-based catalytic process eliminates the need for expensive stoichiometric oxidants and minimizes the formation of over-oxidized by-products. Using a mere 0.5 mol % of the polyether amine 1 as the catalyst, a remarkable > 96% yield was achieved for all 16 tested substrates, encompassing a diverse range of functional groups, under the catalytic aerobic oxidation conditions. Furthermore, it is noteworthy that over 90% of the polyether amine catalyst can be efficiently recovered for reuse without loss of activity, making this a sustainable and cost-effective catalytic approach.

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Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Sun,

Xu,

Yang

et al. 2024

Chemistry An Asian Journal

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In light of the important biological activities and widespread applications of organic disulfides, dithiocarbamates, xanthates, thiocarbamates and thiocarbonates, the continual persuit of efficient methods for their synthesis remains crucial. Traditionally, the preparation of such compounds heavily relied on intricate multi‐step syntheses and the use of highly prefunctionalized starting materials. Over the past two decades, the direct sulfuration of C–H bonds has evolved into a straightforward, atom‐ and step‐economical method for the preparation of organosulfur compounds. This review aims to provide an up‐to‐date discussion on direct C–H disulfuration, dithiocarbamation, xanthylation, thiocarbamation and thiocarbonation, with a special focus on describing scopes and mechanistic aspects. Moreover, the synthetic limitations and applications of some of these methodologies, along with the key unsolved challenges to be addressed in the future are also discussed. The majority of examples covered in this review are accomplished via metal‐free, photochemical or electrochemical approaches, which are in alignment with the overraching objectives of green and sustainable chemistry. This comprehensive review aims to consolidate recent advancements, providing valuable insights into the dynamic landscape of efficient and sustainable synthetic strategies for these crucial classes of organosulfur compounds.

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Recent Catalytic Advances in the Synthesis of Organic Symmetric Disulfides

Cited by 17 publications

References 99 publications

Organic superbase-catalyzed oxidation of alkanethiols to dialkyl disulfides by elemental sulfur

Organic superbase-catalyzed oxidation of alkanethiols to dialkyl disulfides by elemental sulfur

Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

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