- Dess-Martin periodinane mediated synthesis of thioesters from aldehydes
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Dess-Martin periodinane (DMP) mediated efficient synthesis of thioesters from the corresponding aldehydes under mild conditions is described.
- Bandgar, Sunita B.,Bandgar,Korbad,Sawant
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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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- Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
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The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles.
- Li, Guangchen,Rahman, Md. Mahbubur,Szostak, Michal
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p. 1060 - 1066
(2020/04/01)
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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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- Imidazolium-supported benzotriazole: an efficient and recoverable activating reagent for amide, ester and thioester bond formation in water
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An efficient and recyclable imidazolium-supported benzotriazole reagent (Im-CH2-BtH) as a novel synthetic auxiliary has been synthesized and its utility as a carboxyl group activating reagent via the formation of stable imidazolium-supported acyl benzotriazoles was explored for the synthesis of amides, esters and thioesters in water under microwave conditions. The reagent was reused five times without any noticeable loss in activity. It is moisture insensitive and highly stable under thermal and aerobic conditions. The application of imidazolium-supported N-acetyl benzotriazole leads to synthesis of paracetamol on the gram scale under greener conditions in 93% yield.
- Shakoor, S.M. Abdul,Choudhary, Sunita,Bajaj, Kiran,Muthyala, Manoj Kumar,Kumar, Anil,Sakhuja, Rajeev
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p. 82199 - 82207
(2015/10/12)
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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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- Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
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Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.
- Pan, Xiangcheng,Curran, Dennis P.
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supporting information
p. 2728 - 2731
(2014/06/09)
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- Acylation of diselenides and disulfides with N-acylbenzotriazoles promoted by SmI2
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The acylation of diselenides or disulfides with N-acylbenzotriazoles mediated by SmI2 has been achieved successfully without the presence of HMPA, and the corresponding selenolesters or thioesters have been prepared in good yields.
- Tu, Ya Wei,Zhou, Lie Jin,Lv, Xin,Wang, Xiao Xia
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p. 435 - 439
(2014/05/06)
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- Tetraethylammonium bromide-catalyzed oxidative thioesterification of aldehydes and alcohols
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A metal-free, tetraethylammonium bromide-catalyzed oxidative coupling of aldehydes or alcohols with thiophenols or disulfides has been developed. This protocol affords an efficient and inexpensive approach to the synthesis of a wide range of thioesters in high yields. Copyright
- Zhu, Xuebin,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
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supporting information
p. 3558 - 3562
(2014/01/06)
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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 regiospecific phenylthiolation of some organic acids catalyzed by AlCl3 in the presence of excess anhydrous ZnCl2
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Phenylthiolation of some carboxylic acids catalyzed by AlCl3 in the presence of excess dehydrating agent (ZnCl2) has been achieved. Moreover, regiospecificity was tested of some dioic acids and found to be specific at the aliphatic p
- Roy,Sarker, Ashis K.,Mamun, A. H. Al
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experimental part
p. 2158 - 2163
(2010/08/13)
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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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- A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite
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Rongalite promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions.
- Dan, Weixing,Deng, Hongjuan,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 7384 - 7388
(2010/10/02)
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- A new convenient preparation of thiol esters utilizing N-acylbenzotriazoles
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Diverse thiol esters were synthesized in good to excellent yields (76-99%) by reactions of thiophenol, benzyl mercaptan, ethyl mercaptoacetate, and mercaptoacetic acid with N-acylbenzotriazoles under mild conditions. These results demonstrate the utility of N-acylbenzotriazoles as mild S-acylating agents, especially when the corresponding acid chlorides are not readily available.
- Katritzky, Alan R.,Shestopalov, Aleksandr A.,Suzuki, Kazuyuki
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p. 1806 - 1813
(2007/10/03)
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- Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile
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The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer st
- Oh, Hyuck Keun,Woo, So Young,Shin, Chul Ho,Lee, Ikchoon
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p. 849 - 857
(2007/10/03)
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