86763-30-6Relevant academic research and scientific papers
Tunable aryl imidazolium recyclable ionic liquid with dual br?nsted-lewis acid as green catalyst for friedel-crafts acylation and thioesterification
Chen, Wen-Tin,Chou, Shih-Huan,Ho, Wen-Yueh,Hung, Ming-Wei,Lin, Michelle,Lin, Wesley,Lin, Yi-Jyun,Luo, Shun-Yuan,Reddy, Daggula Mallikarjuna,Thul, Mayur,Wu, Hsin-Ru,Wu, Yao-Peng
, (2020/01/28)
Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.
Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
Xuan, Maojie,Lu, Chunlei,Liu, Meina,Lin, Bo-Lin
, p. 7694 - 7701 (2019/06/27)
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%.
One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
Liao, Yen-Sen,Liang, Chien-Fu
, p. 1871 - 1881 (2018/03/23)
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.
Microwave-assisted Synthesis of Thioesters from Aldehydes and Thiols in Water
Jhuang, Huei-Shu,Liu, Yi-Wei,Reddy, Daggula Mallikarjuna,Tzeng, Yong-Ze,Lin, Wei-Yu,Lee, Chin-Fa
, p. 24 - 27 (2017/10/05)
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
Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis
Qiao, Zongjun,Jiang, Xuefeng
supporting information, p. 1550 - 1553 (2016/05/02)
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.
A novel nickel-catalyzed synthesis of thioesters, esters and amides from aryl iodides in the presence of chromium hexacarbonyl
Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham,Nematollahi, Arash,Firouzi, Hamid Reza
, p. 6445 - 6452 (2015/08/11)
This study describes our findings on a novel and cheap NiCl2 catalytic system under ligand-free conditions for the efficient thiocarbonylation, alkoxycarbonylation and amidocarbonylation reactions of aryl iodides in the presence of Cr(CO)6 as the solid source of carbon monoxide under air. A variety of aryl iodides tolerated the reaction conditions and structurally different thiols, alcohols and amines were used efficiently. The corresponding thioesters, esters and amides were obtained in good to excellent yield at atmospheric pressure under mild reaction conditions.
Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions
Zeng, Jing-Wen,Liu, Yi-Chen,Hsieh, Ping-An,Huang, Yu-Ting,Yi, Chih-Lun,Badsara, Satpal Singh,Lee, Chin-Fa
, p. 2644 - 2652 (2014/05/06)
A DTBP-promoted C-H thiolation of aldehydes with disulfides under metal-free and solvent-free conditions is described. The system shows good functional group tolerance to afford thioesters in moderate to excellent yields. the Partner Organisations 2014.
Iron-catalyzed synthesis of thioesters from thiols and aldehydes in water
Huang, Yu-Ting,Lu, Shao-Yi,Yi, Chih-Lun,Lee, Chin-Fa
, p. 4561 - 4568 (2014/06/09)
The preparation of thioesters through the iron-catalyzed coupling reaction of thiols with aldehydes is described. The reactions were carried out by using tert-butyl hydroperoxide (TBHP) as an oxidant and water as a solvent in most cases. This system is co
Palladium-catalyzed fluorocarbonylation using N-formylsaccharin as CO source: General access to carboxylic acid derivatives
Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
, p. 5370 - 5373 (2013/11/06)
N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.
Synthesis of thioesters through copper-catalyzed coupling of aldehydes with thiols in water
Yi, Chih-Lun,Huang, Yu-Ting,Lee, Chin-Fa
, p. 2476 - 2484 (2013/09/12)
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
