- 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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- A novel approach toward thioester bond formation mediated by N,N’ -diisopropylcarbodiimide in water
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A simple and efficient method has been developed for the synthesis of thioesters from carboxylic acids and thiols using N,N'-diisopropylcarbodiimide (DIC). The reactions were carried out in water as an environmentally friendly and green solvent. The devel
- Fattahi, Nadia,Varnaseri, Najmeh,Ramazani, Ali
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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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- Forging C-S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation
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A nickel-catalyzed decarbonylation or decarbonylation accompanied by decarboxylation cross-coupling reaction of aryl anhydrides with thiophenols as coupling partners was disclosed. This method is promoted by a commercially available, moisture-stable, and inexpensive nickel(II) precatalyst. The process can tolerate a variety of functional groups using ubiquitous aryl anhydrides as cross-coupling precursors to produce thioethers in moderate to excellent yields.
- Zhou, Jing-Ya,Tao, Shou-Wei,Liu, Rui-Qing,Zhu, Yong-Ming
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p. 11891 - 11901
(2019/10/11)
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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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- 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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- 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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- 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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- 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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- 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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- Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species
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(Chemical Equation Presented) Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride-MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-α-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O2-CBu t)2 between pivalic anhydride and MoO2Cl 2 as the catalyst.
- Chen, Chien-Tien,Kuo, Jen-Huang,Pawar, Vijay D.,Munot, Yogesh S.,Weng, Shieu-Shien,Ku, Cheng-Hsiu,Liu, Cheng-Yuan
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p. 1188 - 1197
(2007/10/03)
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- Generation of Acyl Radicals from 2-Naphthyl Thioesters
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A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides.Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes.In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields.Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals.The formation of aldehydes was not perturbed by possible Norrish Type II reactions.
- Penn, John H.,Liu, Fang
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p. 2608 - 2612
(2007/10/02)
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