- One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
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In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
- Liao, Yen-Sen,Liang, Chien-Fu
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p. 1871 - 1881
(2018/03/23)
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- Microwave-assisted Synthesis of Thioesters from Aldehydes and Thiols in Water
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We describe the synthesis of thioesters via copper- or iron-catalyzed coupling of thiols with aldehydes on application of microwave irradiation. In this protocol, a variety of aliphatic and aromatic aldehydes and thiols were used, and the products were ob
- Jhuang, Huei-Shu,Liu, Yi-Wei,Reddy, Daggula Mallikarjuna,Tzeng, Yong-Ze,Lin, Wei-Yu,Lee, Chin-Fa
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- Direct oxidative coupling of thiols and benzylic ethers via C(sp3)-H activation and C-O cleavage to lead thioesters
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An unprecedented C-S formation method via direct oxidative C(sp3)-H bond functionalization and C-O cleavage of benzylic ethers was developed. Various thioesters including thioester structure containing drug intermediates could be achieved by th
- Feng,Lv,Lu,Cai
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supporting information
p. 677 - 681
(2015/02/19)
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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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- An odorless, one-pot synthesis of thioesters from organic halides, thiourea and benzoyl chlorides in water
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Thioesterification can be realized via an odorless, one-pot reaction through the in situ generation of S-alkylisothiouronium salts from organic halides and thiourea in aqueous Triton X-100 (TX100) micelles. The protocol is free of foul-smell thiols and or
- Lu, Guo-Ping,Cai, Chun
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supporting information
p. 1271 - 1276
(2013/06/26)
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- Synthesis of thioesters through copper-catalyzed coupling of aldehydes with thiols in water
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Copper-catalyzed C-S bond formation between aldehydes and thiols in the presence of TBHP as an oxidant is described. Functional groups including chloro, trifluoromethyl, bromo, iodo, nitrile, ester and thiophene are all tolerated by the reaction condition
- Yi, Chih-Lun,Huang, Yu-Ting,Lee, Chin-Fa
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p. 2476 - 2484
(2013/09/12)
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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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- A Convenient Synthesis of Thioacetates and Thiobenzoates Using Silica-Gel Supported Potassium Thioacetate
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A simple and efficient procedure has been developed for the synthesis of thioesters by a reaction of alkyl halides with silica-gel supported potassium thioacetate or thiobenzoate under mild conditions.
- Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
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p. 3817 - 3824
(2007/10/03)
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- Sulfur-Extrusive Rearrangement of α-Acylthio Ester by Lithium Amide
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α-Acylthio esters readily undergo facile rearrangement to give β-keto esters on treatment with lithium amide at -78 deg C.Thiolactone 3, a key intermediate for thiolactonic antibiotics, was synthesized by utilizing the rearrangement.
- Tsuzuki, Kazuo,Akeyoshi, Masaharu,Omura, Satoshi
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p. 395 - 396
(2007/10/02)
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- On 1,3-Thiazines, XX: Transacylating N-Acyltetrahydro-1,3-thiazine-2-thiones
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The synthesis of novel N-acyltetrahydro-1,3-thiazine-2-thiones 3 with transacylating activity towards nucleophilic compounds is described.
- Hanefeld, Wolfgang,Bercin, Erdogan
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