- Copper-Mediated, Palladium-Catalyzed Coupling of Thiol Esters with Aliphatic Organoboron Reagents
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Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs2CO3. Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.
- Yu, Ying,Liebeskind, Lanny S.
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Read Online
- Air-stable, cationic, Lewis acid, titanocene perfluorooctanesulfonate- catalyzed reductive cleavage of S-S bond by zinc and its application in synthesis of thioesters
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Titanocene perfluorooctanesulfonate is air-stable complex. In the presence of 10mol% of the complex, reductive cleavage of an S-S bond by zinc in commercial tetrahydrofuran at room temperature led to nucleophilic sulfur anion species, which reacted with acid anhydrides to afford thioesters in good to excellent yields. Copyright
- Qiu, Ren Hua,Xu, Xin Hua,Li, Yin Hui,Shao, Ling Ling,Zhang, Guo Ping,An, De Lie
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Read Online
- Preparation method of thioester compounds
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The invention discloses a preparation method of thioester compounds, wherein the method comprises the following steps: adding nickel trifluoromethanesulfonate, 4,4'-di-tert-butyl-2,2'-dipyridyl, carbonyl molybdenum, potassium carbonate, zinc iodide, water
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Paragraph 0036-0047
(2021/01/29)
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- Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols
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Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].
- Singh, Pallavi,Peddinti, Rama Krishna
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- Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin
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We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.
- Ichihara, Shuta,Ishida, Moeka,Ito, Ryo,Kato, Ayumu,Monguchi, Yasunari,Nakamura, Shinji,Park, Kwihwan,Sajiki, Hironao,Takada, Hitoshi,Wakayama, Fumika,Yamada, Tsuyoshi,Yamada, Yutaro
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p. 2702 - 2710
(2022/01/19)
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- Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
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We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
- Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
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supporting information
p. 8098 - 8103
(2021/10/25)
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- Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
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Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
- Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
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p. 10829 - 10837
(2021/07/28)
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- Conversion of esters to thioesters under mild conditions
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We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.
- Shi, Yijun,Liu, Xuejing,Cao, Han,Bie, Fusheng,Han, Ying,Yan, Peng,Szostak, Roman,Szostak, Michal,Liu, Chengwei
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p. 2991 - 2996
(2021/04/14)
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- Method for synthesizing thioester through cross-coupling of visible light-catalyzed sodium sulfinate and acyl chloride
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The method takes sodium sulfinate and acyl chloride as raw materials and utilizes 2, 6 - dimethyl -1, 4 - dihydro -3, 5 - pyridine dicarboxylic acid diethyl ester and an organic alkali catalytic system to cross-couple sulfur radicals and acyl radicals und
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Paragraph 0016-0019
(2021/09/11)
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- Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
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The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.
- Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
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p. 14653 - 14663
(2020/12/29)
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- Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy
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Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of
- Feng, Yunxia,Yang, Shimin,Zhao, Shen,Zhang, Dao-Peng,Li, Xinjin,Liu, Hui,Dong, Yunhui,Sun, Feng-Gang
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supporting information
p. 6734 - 6738
(2020/09/15)
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- Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters
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An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored. Using Mo(CO)6 as a solid CO surrogate and reductant, a broad range of thioesters were obtained in moderate to good yields with good functional group tolerance.
- Qi, Xinxin,Bao, Zhi-Peng,Yao, Xin-Tong,Wu, Xiao-Feng
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supporting information
p. 6671 - 6676
(2020/09/02)
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- Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters
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A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters.
- Bogonda, Ganganna,Patil, DIlip V.,Kim, Hun Young,Oh, Kyungsoo
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supporting information
p. 3774 - 3779
(2019/05/24)
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- Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
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Direct thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.
- Xuan, Maojie,Lu, Chunlei,Liu, Meina,Lin, Bo-Lin
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p. 7694 - 7701
(2019/06/27)
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- Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation
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An efficient and convenient strategy for the preparation of diaryl sulfides via a Fe-promoted direct sulfuracylation of 2-naphthylamine using thioesters as bifunctional reagents is described. This synthetic strategy features high chemoselectivity, good substrate scope and functional group tolerance. (Figure presented.).
- Xiao, Fuhong,Yuan, Shanshan,Wang, Dahan,Liu, Saiwen,Huang, Huawen,Deng, Guo-Jun
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supporting information
p. 3331 - 3336
(2019/06/13)
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- Na2CO3-promoted thioesterification via N–C bond cleavage of amides to construct thioester derivatives
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A mild, efficient, and transition-metal-free catalytic strategy is developed to construct thioesters via selective N–C bond cleavage of Boc2-activated primary amides. This strategy is successfully carried out with stoichiometric Na2C
- Tao, Jiasi,Yu, Weijie,Luo, Jin,Wang, Tao,Ge, Wanling,Zhang, Ziwei,Yang, Bingjie,Xiong, Fei
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p. 486 - 492
(2019/11/03)
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- Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters
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A method for Ni-catalyzed controlled decarbonylation of α-ketothioesters is described. Mono- and double-decarbonylations, which gave thioesters and thioethers, respectively, were selectively achieved by changing the ligand. A fundamental study of Ni-catalyzed decarbonylation of α-ketothioesters is presented.
- Zheng, Zhao-Jing,Jiang, Cheng,Shao, Peng-Cheng,Liu, Wen-Fei,Zhao, Tian-Tian,Xu, Peng-Fei,Wei, Hao
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p. 1907 - 1910
(2019/05/02)
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- Metal-free thioesterification of amides generating acyl thioesters
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A base-initiated thioesterification of amides with various thiols is reported. This reaction can take place efficiently under metal-free and air-atmospheric conditions, and provides a facile and practically useful approach to the synthesis of valuable acy
- Wang, Qun,Liu, Long,Dong, Jianyu,Tian, Zhibin,Chen, Tieqiao
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supporting information
p. 9384 - 9388
(2019/06/21)
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- Preparation method and application of novel ionic binuclear Schiff base titanium complex
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The invention provides a preparation method of a novel ionic binuclear Schiff base titanium complex and a synthetic method of applying the novel ionic binuclear Schiff base titanium complex to catalyze zinc powder and reduce disulfide or selenide to prepare sulfo(seleno) ester and dissymmetric sulfoether(selenide). The complex is a cationic binuclear Schiff base titanium complex, wherein titaniumatoms are bridged by oxygen atoms and are coordinated with a Schiff base ligand and a hydrone, and an ionic bond is formed by a cation part and an anion part of whole Schiff base titanium. The ionic binuclear Schiff base titanium complex is used as a catalyst, the zinc powder is used as a reducer, the disulfide(selenide) can be reduced and fractured, and the disulfide(selenide) can further and respectively react with anhydride, an alpha-bromo carbonyl compound and bromoalkane to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide). According to the preparation method provided by the invention, the defects that traditional lewis acid halide is deliquescent, an absolute solvent is used, conditions are strict and the like are overcome; an effective path for reducing the disulfide or selenide to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide) is provided, and the preparation method has the advantages of high yield, simpleness in operation andthe like.
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Paragraph 0054; 0055
(2018/04/03)
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- Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters
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A novel, efficient, metal-, base- and acid-free straightforward protocol has been developed for the construction of useful thioesters. The immense catalytic potential of HFIP for promoting the thiocarbonylation of acyl halides and thiols is disclosed. HFIP was recovered with ease and reused for further reactions without any loss of reactivity. Both aryl and alkyl thiols bearing electron-donating and electron-withdrawing groups as well as aryl- and alkyl acyl halides worked well in this reaction. Inexpensive precursors, short reaction time, obviating workup, high atom economy, and gram-scale preparation are the significant features of the developed eco-friendly route for S-carbonylation of thiols.
- Singh, Pallavi,Peddinti, Rama Krishna
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supporting information
p. 1875 - 1878
(2017/04/21)
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- One for Many: A Universal Reagent for Acylation Processes
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This work describes acylation reactions facilitated by a type of heterocycle-based acyl transfer agent, 2-acyloxypyridazinone. Reactions of 2-acyloxypyridazinone with carboxylic acids yield mixed carbonic anhydride intermediates, which are reactive and could be coupled with a wide range of substrates including acids, amines, alcohols, and thiols. The wide substrate scope, ease of operation (no additive or catalyst), storage and handling stability, and atom-efficiency from recycling the heterocycle carrier make the reported acylating agent attractive for acylation-based coupling reactions.
- Moon, Hyun Kyung,Sung, Gi Hyeon,Kim, Bo Ram,Park, Jong Keun,Yoon, Yong-Jin,Yoon, Hyo Jae
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supporting information
p. 1725 - 1730
(2016/06/09)
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- Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis
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A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was obtained under ligand-free conditions in which disulfide generated from homocoupling could be prevented. Meanwhile, application of bidentate phosphine ligands under carbon monoxide atmosphere (CO balloon) afforded the thioester with little decomposition, which was revealed through interval NMR tracking.
- Qiao, Zongjun,Jiang, Xuefeng
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supporting information
p. 1550 - 1553
(2016/05/02)
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- Poly(3,4-dimethyl-5-vinylthiazolium)/DBU-catalyzed thioesterification of aldehydes with thiols
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Poly(3,4-dimethyl-5-vinylthiazolium) was synthesized from 3,4-dimethyl-5-vinylthiazole through free radical polymerization and was examined as polymer precatalysts in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the thioesterification of aldehydes with thiols. The poly(5-vinylthiazolium)/DBU had excellent catalytic activity and could be reused 10 times without a considerable loss of activity. To S-um up: Poly(3,4-dimethyl-5-vinylthiazolium) is examined as a polymer precatalyst in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the thioesterification of aldehydes with thiols. The poly(5-vinylthiazolium)/DBU system shows excellent catalytic activity and can be reused 10 times without a considerable loss of activity.
- Chung, Junyong,Seo, Ue Ryung,Chun, Supill,Chung, Young Keun
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p. 318 - 321
(2016/02/05)
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- Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters
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A novel, efficient, and catalyst-free strategy has been initially developed for the construction of thioesters via the direct radical oxidative decarboxylation of α-keto acids with thiols, and the corresponding target products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse thioesters.
- Yan, Kelu,Yang, Daoshan,Wei, Wei,Zhao, Jing,Shuai, Yuanyuan,Tian, Laijin,Wang, Hua
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p. 7323 - 7330
(2015/07/01)
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- Formation of C(sp2)-S bonds through decarboxylation of α-oxocarboxylic acids with disulfides or thiophenols
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Copper-catalyzed decarboxylative coupling between α-oxocarboxylic acids and diphenyl disulfides or thiophenols is presented, which provided an effective and direct approach for the preparation of useful thioesters through C(sp2)-S bond formatio
- Rong, Guangwei,Mao, Jincheng,Liu, Defu,Yan, Hong,Zheng, Yang,Chen, Jie
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p. 26461 - 26464
(2015/03/30)
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- Iron-catalyzed thioesterification of methylarenes with thiols in water
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An iron-catalyzed coupling reaction of methylarenes with thiols leading to thioesters has been developed. The reactions were carried out in water with tert-butyl hydroperoxide (TBHP) as the oxidant and polyoxyethanyl α-tocopheryl sebacate (PTS) as the sur
- Wang, Liang,Cao, Jing,Chen, Qun,He, Ming-Yang
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supporting information
p. 7190 - 7193
(2015/01/16)
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- Selective approach to thioesters and thioethers via sp3 C-H activation of methylarenes
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Novel C-S cross-dehydrogenative coupling (CDC) approaches for the selective synthesis of thioesters and thioethers have been developed via sp3 C-H activation of methylarenes and subsequent functionalization. The reaction of methylarenes with thiols resulted in thioesters in the presence of a FeBr2/TBHP system, while treatment of methylarenes with thiols in the Pd(OAc)2/O2/TBHP system led to the formation of thioethers. Both the green protocols demonstrate good functional group tolerance and satisfactory yields. This journal is
- Feng,Lu,Cai
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p. 54409 - 54415
(2015/01/16)
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- Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
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Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields. Compared with the previous method, the present route is very simple, atom-economical and environmentally friendly. This journal is the Partner Organisations 2014.
- He, Chunhuan,Qian, Xuewei,Sun, Peipei
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supporting information
p. 6072 - 6075
(2014/08/05)
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- Reductive coupling of disulfides and diselenides with alkyl halides catalysed by a silica-supported phosphine rhodium complex using hydrogen as a reducing agent
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The reductive coupling of disulfides and diselenides with alkyl halides was achieved in THF at 65 °C in the presence of 3 mol% of a silica-supported phosphine rhodium complex and triethylamine using hydrogen as a reducing agent, affording a variety of unsymmetrical sulfides and selenides in high yields. The heterogeneous rhodium catalyst can be recovered by a simple filtration and reused several times without significant loss of activity. Reaction with an acyl halide was also observed.
- Zhang, Hean,Hu, Mangen,Cai, Mingzhong
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p. 645 - 647
(2013/11/06)
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- Oxidative folding of lysozyme with aromatic dithiols, and aliphatic and aromatic monothiols
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In vitro protein folding of disulfide containing proteins is aided by the addition of a redox buffer, which is composed of a small molecule disulfide and/or a small molecule thiol. In this study, we examined redox buffers containing asymmetric dithiols 1-5, which possess an aromatic and aliphatic thiol, and symmetric dithiols 6 and 7, which possess two aromatic thiols, for their ability to fold reduced lysozyme at pH 7.0 and 8.0. Most in vivo protein folding catalysts are dithiols. When compared to glutathione and glutathione disulfide, the standard redox buffer, dithiols 1-5 improved the protein folding rates but not the yields. However, dithiols 6 and 7, and the corresponding monothiol 8 increased the folding rates 8-17 times and improved the yields 15-42% at 1 mg/mL lysozyme. Moreover, aromatic dithiol 6 increased the in vitro folding yield as compared to the corresponding aromatic monothiol 8. Therefore, aromatic dithiols should be useful for protein folding, especially at high protein concentrations.
- Patel, Amar S.,Lees, Watson J.
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scheme or table
p. 1020 - 1028
(2012/03/10)
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- The direct thioesterification of aldehydes with disulfides via NHC-catalyzed carbonyl umpolung strategy
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An efficient N-heterocyclic carbene (NHC)-catalyzed direct thioesterification of aldehydes and α,β-unsaturated aldehydes (enals) with diaryl disulfides is reported. The protocol involves carbonyl umpolung reactivity of aldehydes and enals in which the car
- Singh, Santosh,Yadav, Lal Dhar S.
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experimental part
p. 5136 - 5140
(2012/09/22)
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- Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement
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In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of keto
- Arisawa, Mieko,Kuwajima, Manabu,Toriyama, Fumihiko,Li, Guangzhe,Yamaguchi, Masahiko
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supporting information; experimental part
p. 3804 - 3807
(2012/09/07)
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- Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
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Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.
- Arisawa, Mieko,Igarashi, Yui,Kobayashi, Haruki,Yamada, Toru,Bando, Kentaro,Ichikawa, Takuya,Yamaguchi, Masahiko
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supporting information; experimental part
p. 7846 - 7859
(2011/10/12)
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- Dynamic covalent chemistry of disulfides offers a highly efficient synthesis of diverse benzofused nitrogen-sulfur heterocycles in one pot
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The thiol-disulfide dynamic interchange reaction mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was extensively studied. By this synthetic method sulfides can be prepared successfully within seconds in high yields at room temperature from stable and readily available disulfides and an alkylating agent. The method was further demonstrated to efficiently produce benzofused nitrogen-sulfur heterocycles with high skeletal diversity in a one-pot process.
- Zhu, Ning,Zhang, Fa,Liu, Gang
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scheme or table
p. 531 - 540
(2010/09/05)
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- Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
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A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh 3)4-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6- tetrafluorobenzenes.
- Arisawa, Mieko,Yamada, Toru,Yamaguchi, Masahiko
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supporting information; experimental part
p. 6090 - 6092
(2011/01/04)
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- Silica-promoted facile synthesis of thioesters and thioethers: A highly efficient, reusable and environmentally safe solid support
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An efficient, mild and rapid procedure for the acylation and alkylation of aromatic and aliphatic thiols mediated on a silica gel surface at room temperature is described. The protocol allows the protection of thiols under neutral heterogeneous conditions without requiring any bases or Lewis acids, and the silica gel used as the promoter can be recycled for several runs without any loss of activity.
- Basu, Basudeb,Paul, Susmita,Nanda, Ashis K.
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experimental part
p. 767 - 771
(2010/09/05)
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- An approach to the synthesis of thioesters and selenoesters promoted by rongalite?
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Rongalite? promotes cleavage of diaryldisulfides generating the corresponding chalcogenolate anions that then undergo facile reaction with N-acylbenzotriazoles in the presence of K2CO3 to afford thioesters in good to excel
- Lin, Shao-Miao,Zhang, Ji-Lei,Chen, Jiu-Xi,Gao, Wen-Xia,Ding, Jin-Chang,Su, Wei-Ke,Wu, Hua-Yue
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experimental part
p. 1616 - 1620
(2010/11/17)
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- Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids
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(Chemical Equation Presented) Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.
- Cao, Hong,McNamee, Laura,Alper, Howard
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p. 3530 - 3534
(2008/09/20)
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- Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst
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A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.
- Bandgar, Babasaheb Pandurang,More, Parmeshwar Eknath,Kamble, Vinod Tribhuvannathji,Sawant, Sanjay Suresh
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experimental part
p. 1006 - 1010
(2009/04/05)
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- Rate enhancement of the oxidative folding of lysozyme by the use of aromatic thiol containing redox buffers
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Almost all therapeutic proteins and most extracellular proteins contain disulfide bonds. The production of these proteins in bacteria or in vitro is challenging due to the need to form the correctly matched disulfide bonds during folding. One important pa
- Gurbhele-Tupkar, Minakshi C.,Perez, Lissette R.,Silva, Yenia,Lees, Watson J.
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p. 2579 - 2590
(2008/12/21)
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- Thioimides: New reagents for effective synthesis of thiolesters from carboxylic acids
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(Chemical Equation Presented) Thioimides and carboxylic acids are used as the precursors for the convenient synthesis of thiolesters in the phosphine mediated process. Cyclic and acyclic thioimides show equal efficiency, furnishing the desired thiolesters in good to excellent yields. The general, highly efficient transformation tolerates various functional groups and the resulting thiolesters are obtained in high purity after a simple separation. The reaction scope has been demonstrated on the preparation of several highly functionalized target molecules.
- Henke, Adam,Srogl, Jiri
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p. 7783 - 7784
(2008/12/22)
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- KF/Al2O3 catalysed synthesis of thiol esters from N-acylphthalimides and thiols
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A new method for the preparation of thiol esters from N-acylphthalimides and thiols in the presence of KF/Al2O3 is introduced.
- Movassagh, Barahman,Zakinezhad, Yousef
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p. 369 - 370
(2007/10/03)
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- Efficient copper-catalyzed coupling of aryl iodides and thiobenzoic acid
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A highly efficient copper-catalyzed coupling reaction of aryl iodides and thiobenzoic acid, using 10 mol % of copper iodide, 20 mol % of 1,10-phenanthroline, and iPr2NEt in toluene, was developed. This methodology is applicable to a variety of aryl iodides.
- Sawada, Naotaka,Itoh, Takahiro,Yasuda, Nobuyoshi
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p. 6595 - 6597
(2007/10/03)
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- CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
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Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
- Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
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p. 1583 - 1589
(2007/10/03)
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- Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
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(Chemical Equation Presented) We have established that RhCl(PPh 3)3 catalyzes a reductive coupling of disulfides and diselenides with alkyl halides in the presence of triethylamine using hydrogen as a reducing agent. This reaction serves as a convenient new method to produce unsymmetrical sulfides and selenides from disulfides and diselenides instead of unstable and odoriferous thiols and selenols.
- Ajiki, Kaori,Hirano, Masao,Tanaka, Ken
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p. 4193 - 4195
(2007/10/03)
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- 3,6-Dibenzoxyl-1,2-pyridazine: A new versatile benzoyl transferring agent for NH2, -OH and -SH benzoylations
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A newly synthesized 3,6-dibenzoxyl-1,2-pyridazine 3 has been investigated for its potential to transfer the benzoyl group to various organic substrates carrying -NH2, -OH and -SH groups. The benzoyl transfer is fairly general in scope, occurs under convenient conditions and provides good to excellent yields of benzoylated products. Moreover, by choosing proper conditions, it is possible to achieve chemoselective benzoylation in bi-functional molecules. For instance, N-benzoylation of aromatic amines can be selectively accomplished over that of aliphatic amines and vice versa by manipulating reaction conditions. Selective N- or O-benzoylation in aminophenols is also possible. Although, not studied in detail, we final that dibenzoate 3 can also be used to effect C-benzoylation of reactive phenols and ketones, as exemplified by the C-benzoylation of resorcinol and acetophenone, respectively. Dibenzoate 3, besides being a crystalline, easy to handle, solid possesses twice the potential as an acyl carrier compared to the other known acyl carriers. These features make 3 as an attractive choice for many applications pertaining to benzoyl transfer reactions.
- Mashraqui, Sabir Hussain,Shivaji, Jadhav Latika
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p. 927 - 935
(2007/10/03)
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- An improved, general procedure to S-aryl thiol esters: A new synthetic application of dry arenediazonium o-benzenedisulfonimides
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The reaction between dry arenediazonium o-benzenedisulfonimides (1) and sodium thioacetate or thiobenzoate in anhydrous acetonitrile at room temperature is an efficient and safe procedure, of general validity, for the preparation of S-aryl thiol esters. The products can be easily purified and the yields are always very high. Of the 28 considered examples, the average yield of the S-aryl thioacetates (7) was 86% and that of the S-aryl thiobenzoates (8) 88%. It was possible to recover, in good amount and from all the reactions, o-benzenedisulfonimide (9), reusable for the preparation of salts 1.
- Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita
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p. 1225 - 1230
(2007/10/03)
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- Convenient synthesis of thiol esters from acyl chlorides and disulfides using Zn/AlCl3
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Various thiol esters were prepared by condensation of acyl chlorides with disulfides in the presence of Zn/AlCl3. The advantages of this method are high yields under relatively mild conditions, simple work-up, lack of toxicity, and low costs.
- Lakouraj, Moslem M.,Movassagh, Barahman,Fadaei, Zahra
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p. 1085 - 1088
(2007/10/03)
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- A convenient one-pot synthesis of thiol esters from disulfides using a Zn/AlCl3 system
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A novel synthetic procedure for the direct preparation of thiol esters from various disulfides and symmetrical anhydrides using a Zn/AlCl3 system is described.
- Movassagh,Lakouraj,Fadaei
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- Hypervalent iodine in synthesis 56: A convenient route for the synthesis of thiol esters via palladium-catalysed alkylthiocarbonylation or arylthio-carbonylation of diaryliodonium salts
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Palladium-catalysed alkylthiocarbonylation or arylthiocarbonylation of diaryliodonium salts gives thiol esters in good yields.
- Wang,Chen
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p. 372 - 373
(2007/10/03)
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