1484-17-9Relevant academic research and scientific papers
Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage
Lu, Kui,Lv, Ming-Xiu,Mai, Wen-Peng,Sui, Hong-Da
, p. 890 - 895 (2021/07/02)
Aryl thioesters are synthesized via nickel-catalyzed carbonylation of thioacetates with aryl iodides. Alkyl thioacetates undergo coupling with carbon monoxide and aryl iodides to produce the desired aryl thioesters in moderate yields. This catalytic carbonylative coupling process provides a cost-effective and direct approach for the preparation of useful thioesters.
Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters
Qi, Xinxin,Bao, Zhi-Peng,Yao, Xin-Tong,Wu, Xiao-Feng
supporting information, p. 6671 - 6676 (2020/09/02)
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.
Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
Steemers, Luuk,Wijsman, Linda,van Maarseveen, Jan H.
supporting information, p. 4241 - 4245 (2018/10/02)
Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).
Microwave-assisted direct thioesterification of carboxylic acids
Chou, Yen-Lin,Jhong, Yi,Swain, Sharada Prasanna,Hou, Duen-Ren
, p. 10201 - 10208 (2018/05/31)
A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.
Investigations of the Thermal Responsiveness of 1,4,2-Oxathiazoles
Hewitt, Russell J.,Ong, Michelle Jui Hsien,Lim, Yi Wee,Burkett, Brendan A.
supporting information, p. 6687 - 6700 (2015/10/29)
The first systematic study of the thermal rearrangement/fragmentation of 5,5-disubstituted 1,4,2-oxathiazoles into isothiocyanates is reported. Structure-activity relationships reveal that the choice of substituent at the 5-position of the 1,4,2-oxathiazoles is the predominant factor to influence the ease of fragmentation.
Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
He, Chunhuan,Qian, Xuewei,Sun, Peipei
supporting information, p. 6072 - 6075 (2014/08/05)
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.
Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl- thiazolin-2-thione derivatives. Part III: An alkylthiol- and thioacid-free route to diversely substituted S-alkyl thioesters
Mehdid, Mohammed Amine,Djafri, Ayada,Andreoli, Federico,Vanthuyne, Nicolas,Farran, Daniel,Niebler, Johannes,Buettner, Andrea,Giorgi, Michel,Roussel, Christian
, p. 4994 - 5001 (2013/07/19)
A metal free synthesis of S-alkyl thioesters, which does not involve alkylthiol or thiocarboxylic acid as sulfur source is disclosed. The process involves first an acylation at the nitrogen of the readily available N-(2-aminophenyl)-4-methyl-thiazolin-2-thione, second an alkylation at sulfur of the resulting amides and finally a base catalyzed metathetic reaction, which provides under very mild conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1] benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments. S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle.
Highly efficient iron(II) chloride/N-bromosuccinimide-mediated synthesis of imides and acylsulfonamides
Wang, Feng,Liu, Hongxia,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
supporting information; experimental part, p. 246 - 252 (2009/09/05)
We have developed a general and highly efficient iron(II) chloride/N-bromosuccinimide (NBS)-mediated method for the synthesis of imides and acylsulfonamides via couplings of thioesters with carboxamides/sulfonamides, and the method is simple, economical and shows practical advantages.
Synthesis of thioesters by simultaneous activation of carboxylic acids and alcohols using PPh3/NBS with benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent
Gopinath, Purushothaman,Vidyarini, Ravindran Sasitha,Chandrasekaran, Srinivasan
experimental part, p. 6043 - 6047 (2010/03/25)
A new and simple route for the synthesis of thioesters starting from carboxylic acids and alcohols is reported by using tetrathiomolybdate as the key sulfur transfer reagent, Triphenylphosphane and N-bromosuccinimide were used for the activation of the ca
Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst
Bandgar, Babasaheb Pandurang,More, Parmeshwar Eknath,Kamble, Vinod Tribhuvannathji,Sawant, Sanjay Suresh
experimental part, p. 1006 - 1010 (2009/04/05)
A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.
