- 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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- Manganese(iii)-promoted thiocarbonylation of alkylborates with disulfides: synthesis of aliphatic thioesters
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A Mn(iii)-promoted thiocarbonylation procedure toward the synthesis of thioesters has been developed. By employing easily available disulfides and potassium alkyltrifluoroborates as the starting materials, and cheap and non-toxic Mn(OAc)3·2H2O as the promotor, a broad range of thioesters were synthesized in good to excellent yieldsviaradical intermediates.
- Chen, Bo,Wu, Xiao-Feng
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supporting information
p. 9654 - 9658
(2021/12/01)
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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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- Synthesis of Thioethers and Thioesters with Alkyl Arylsulfinates as the Sulfenylation Agent under Metal-Free Conditions
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A study on the coupling of cycloalkanes with alkyl arylsulfinates has been performed. Using iodine as the catalyst, through C (Formula presented.) ?H bond activation and sulfinates reduction, a wide range of thioethers were produced in moderate to high yields. Additionally, various thiocarboxylic esters can also be produced by simply performing the reaction under CO pressure. Notably, this is the first report in which alkyl arylsulfinates were used as sulfenylation agents in a cross-coupling transformation.
- Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 3503 - 3507
(2016/12/26)
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- Beta-lactones as antibacterial agents
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The present invention relates to specific beta-lactone compounds and compositions thereof for the treatment of infections, such as, e.g., infections with bacteria or infections with protozoa, in particular infections with Gram-positive and/or Gram-negativ
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Page/Page column 37-39
(2017/01/05)
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- Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
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A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.
- Banerjee, Subhash,Adak, Laksmikanta,Ranu, Brindaban C.
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supporting information; experimental part
p. 2149 - 2152
(2012/05/05)
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- Synthesis of acylsilanes by palladium-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides
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An acylsilane synthesis by a Pd-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides was developed. S-Phenyl thiol esters with a variety of functional groups were converted to corresponding acylsilanes.
- Azuma, Hiroki,Okano, Kentaro,Tokuyama, Hidetoshi
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supporting information; experimental part
p. 959 - 961
(2011/12/05)
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- Rapid and convenient thioester synthesis under phase-transfer catalysis conditions
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Various thioesters were obtained through an efficient phase-transfer catalysis method, by treating several thiophenols with different acyl chlorides, in a biphasic system composed of 10% aqueous NaOH and dichloromethane in the presence of tetrabutylammonium chloride. The thiolation reaction was complete in only 5 minutes, at 0C. Taylor & Francis Group, LLC.
- Simion, Cristian,Hashimoto, Iwao,Mitoma, Yoshiharu,Simion, Alina Marieta,Egashira, Naoyoshi
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experimental part
p. 2480 - 2488
(2011/02/23)
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- Silica nanoparticles as a reusable catalyst: A straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts under neutral reaction conditions
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A simple and straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts has been demonstrated using silica nanoparticles (NPs) as a reusable catalyst via the 1,2-addition of thiols to alkenes, alkynes and alkyl/acyl halides, and the 1,4-addition of thiols to conjugated alkenes at room temperature.
- Banerjee, Subhash,Das, Jayanta,Alvarez, Richard P.,Santra, Swadeshmukul
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experimental part
p. 302 - 306
(2010/06/13)
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- β-lactones as privileged structures for the active-site labeling of versatile bacterial enzyme classes
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(Chemical Equation Presented) A chemical proteomic strategy has been applied directly to bacterial proteomes, and b-lactones have been identified as important natural product derivatives with a high affinity to various enzyme classes (see picture). This a
- Boettcher, Thomas,Sieber, Stephan A.
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supporting information; experimental part
p. 4600 - 4603
(2009/02/08)
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- A convenient method for the synthesis of carboxamides and thioesters by using tetrakis(2-methylimidazol-1-yl)silane
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Tetrakis(2-methylimidazol-1-yl)silane [Si(2-Me-Im)4], a new dehydrating reagent having silicon-imidazole linkage, reacted readily with carboxylic acids at room temperature to form the corresponding 1-acyl-2-methylimidazole intermediates, which smoothly underwent subsequent condensation with nucleophiles such as amines or thiols to afford the corresponding carboxamides or thioesters in good to excellent yields, respectively.
- Tozawa, Takashi,Yamane, Yoshinobu,Mukaiyama, Teruaki
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p. 629 - 641
(2007/10/03)
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- Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br
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An easily accessible and inexpensive room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes the reaction of alkyl halides or acyl halides with thiols without any solvent at room temperature leading to the synthesis of thioethers and thioesters in high yields. This reaction has also been extended for the preparation of dithianes and transthioetherification. The ionic liquid is recovered and recycled for subsequent runs.
- Ranu, Brindaban C.,Jana, Ranjan
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p. 1811 - 1818
(2007/10/03)
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- Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters
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Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 5793 - 5795
(2007/10/03)
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- Radical reaction of S-phenyl chlorothioformate with alkyl iodides: Free radical-mediated carboxylation approach
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Free radical-mediated carboxylation is achieved by treatment of alkyl iodides with S-phenyl chlorothioformate and bis(tributyltin) with irradiation at 300 nm.
- Kim, Sunggak,Jon, Sang Yong
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p. 815 - 816
(2007/10/03)
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- A HIGHLY CONVENIENT PROCEDURE FOR THE HYDROLYSIS OF TERMINAL PHENYL VINYL SULFIDES
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Terminal vinyl and chlorovinyl sulfides are hydrolyzed by 70percent perchloric acid-thiophenol in benzene to the corresponding diphenyl thioacetals and thioesters in good yields.
- Reutrakul, Vichai,Poochaivatananon, Patcharin
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p. 535 - 536
(2007/10/02)
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- A SIMPLE SYNTHESIS OF THIOL ESTERS FROM COPPER-I-MERCAPTIDES AND ACYL CHLORIDES
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Thiol esters are obtained from acyl chlorides and copper-I-mercaptides in excellent yields.
- Reissig, Hans-Ulrich,Scherer, Bernadette
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p. 4259 - 4262
(2007/10/02)
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- Direct transformation of carboxyclic acids to thiol esters induced by phenyl dichlorophosphate
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The condensation of carboxylic acids and thiols is greatly facilitated by the use of phenyl dichlorophosphate as an activating agent giving thiol esters in good yields.
- Liu, Hsing-Jang,Sabesan, Subramaniam Iyer
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p. 2645 - 2648
(2007/10/02)
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