52252-61-6Relevant academic research and scientific papers
Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides
Jiang, Min,Li, Haifang,Yang, Haijun,Fu, Hua
supporting information, p. 874 - 879 (2017/01/14)
The formation of aryl C?S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.
Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: Arene functionalization with activating group recycling
Hooper, Joel F.,Chaplin, Adrian B.,Gonzalez-Rodriguez, Carlos,Thompson, Amber L.,Weller, Andrew S.,Willis, Michael C.
supporting information; experimental part, p. 2906 - 2909 (2012/03/27)
A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.
Microwave-promoted TBAF-catalyzed SNAr reaction of aryl fluorides and ArSTMS: An efficient synthesis of unsymmetrical diaryl thioethers
Liu, Chuanzhi,Zang, Xufeng,Yu, Baohua,Yu, Xiaochun,Xu, Qing
supporting information; experimental part, p. 1143 - 1148 (2011/07/09)
Microwave irradiation was found to promote tetrabutylammonium fluoride catalyzed nucleophilic aromatic substitution of aryl fluorides and arylthiotrimethylsilanes, affording high yields of unsymmetrical diaryl thioethers efficiently under mild, transition-metal- and base-free conditions. Microwave showed unusual improvement on the reaction in not only the conditions and reaction rate, but also in selectivity and substrate scope. Georg Thieme Verlag Stuttgart - New York.
Thermal decomposition of tert-butyl ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)phenyliminoxyperacetates: The reactivity of thio-substituted iminyl radicals
Leardini,McNab,Minozzi,Nanni
, p. 1072 - 1078 (2007/10/03)
Some ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)-substituted phenyliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The sulfanyl-substituted iminyls showed no tendency to give either 1,7- or 1,
Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals
Creed,Leardini,McNab,Nanni,Nicolson,Reed
, p. 1079 - 1085 (2007/10/03)
Flash vacuum pyrolysis (FVP) of the oxime ethers 12-14 and of the sulfides 18-20 at 650°C (10-2-10-3 Torr) gave products derived from the corresponding iminyl and thiophenoxyl radicals. In all cases, benz[d]isothiazoles (e.g., 26) are formed as major products via SHi mechanisms though the yields are greatest with the iminyl precursors. Alternative pathways observed from the thiophenoxyls in specific cases include the formation of the anilinobenzothiophene 36 and of dibenzothiophene 23, via an SHi process and a spirodienyl rearrangement, respectively. There is no evidence for signicant interconversion of the iminyl and thiophenoxyl species.
10-Thia-anthracenes. Part 3. A Re-examination of the Reaction of 9-Phenylthioxanthylium Salt and Phenyl-lithium
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Ban, Masatoshi,Matsushita, Hitoshi
, p. 187 - 194 (2007/10/02)
Reaction of 9-phenylthioxanthylium salt (1) with phenyl-lithium afforded eight compounds, 9-phenyl- (2), 9,9-diphenyl- (3). 3,9-diphenyl (4), 3,9,9-triphenyl- (5), and 4,9,9-triphenyl-thioxanthene (6), 9,9'-diphenyl-9,9'-bithioxanthenyl (7), thioxanthone (8), and 9,9'-diphenyldithioxanth-9-yl peroxide (9).Their structures were determined by comparison with the authentic samples.Six samples, (3)-(6), 2,9,9-triphenyl- (30), 9-(biphenyl-4-yl)-9-phenylthioxanthene (31) were independently synthesized in order to determine the structures of two pairs of positional isomers, 3,4, and 5,6.A radical mechanism contributed to the reaction of compound (1) with phenyl-lithium.
