63107-77-7Relevant academic research and scientific papers
Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
, p. 2447 - 2458 (2020/04/15)
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
Synthesis of diverse phenothiazines by direct thioamination of arynes with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination
Matsuzawa, Tsubasa,Uchida, Keisuke,Yoshida, Suguru,Hosoya, Takamitsu
, p. 825 - 828 (2018/07/05)
A facile method for the synthesis of diverse phenothiazines has been achieved by direct thioamination of aryne intermediates with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination. Since various sulfilimines could be prepared easily by odorless copper-catalyzed ipso-thiolation of readily available o-bromoarylboronic acids followed by imination and hydrolysis, this approach enables the synthesis of a wide variety of multisubstituted phenothiazines.
Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides
Ding, Xiaomei,Huang, Manna,Yi, Zhou,Du, Dongchen,Zhu, Xinhai,Wan, Yiqian
, p. 5416 - 5423 (2017/05/25)
A general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between -OH and -NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv).
Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines
Huang, Manna,Huang, Dongting,Zhu, Xinhai,Wan, Yiqian
supporting information, p. 4835 - 4839 (2015/08/03)
A method for the one-pot synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides was explored. Preliminary work on the mechanism of the reaction suggested that it follows a domino process, including the hydrolysis of benzothiazoles followed by C-S coupling and C-N coupling. The low loading of the catalyst system (5 mol-% for both copper and ligand), the mild experimental conditions (90 °C, 12 h), and the use of a green reaction medium make this synthesis very attractive to academia and industry. A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C-S and C-N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.
Iron-catalyzed S-arylation of benzothiazole with aryl iodides under aqueous medium: Facile synthesis of aryl(2-aminoaryl) sulfides
Lee, Hang Wai,Yung, Ka Fu,Kwong, Fuk Yee
supporting information, p. 2743 - 2747 (2015/01/08)
A simple route for facile access of aryl(2-aminoaryl) sulfide was reported. With the aid of iron(III) chloride catalyst and diamine ligand, benzothiazole was efficiently S-arylated with various aryl iodides (19 examples) in water under air atmosphere. This operationally simple protocol provides aryl(2-aminoaryl) sulfides in moderate to good yields.
Iron-Catalyzed S-Arylation of Benzothiazole with Aryl Iodides under Aqueous Medium: Facile Synthesis of Aryl(2-aminoaryl) Sulfides
Lee, Hang Wai,Yung, Ka Fu,Kwong, Fuk Yee
, p. 2743 - 2747 (2015/05/05)
A simple route for facile access of aryl(2-aminoaryl) sulfide was reported. With the aid of iron(III) chloride catalyst and diamine ligand, benzothiazole was efficiently S-arylated with various aryl iodides (19 examples) in water under air atmosphere. This operationally simple protocol provides aryl(2-aminoaryl) sulfides in moderate to good yields.
Copper oxide nanoparticles supported on graphene oxide-Catalyzed S-arylation: An efficient and ligand-free synthesis of aryl sulfides
Kamal, Ahmed,Srinivasulu, Vunnam,Murty,Shankaraiah, Nagula,Nagesh, Narayana,Reddy, T. Srinivasa,Subba Rao
, p. 2297 - 2307 (2013/10/01)
Copper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand-free and solvent-free C-S cross-coupling reactions with weak bases such as tri- ethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade C-S and C-N cross-coupling of ortho-dihalides and ortho-aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E-factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.
Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution
Feng, Yi-Si,Qi, Hong-Xia,Wang, Wei-Cheng,Liang, Yu-Feng,Xu, Hua-Jian
supporting information; experimental part, p. 2914 - 2917 (2012/07/27)
A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50°C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield.
Assembly of substituted phenothiazines by a sequentially controlled CuI/L-proline-catalyzed cascade C-S and C-N bond formation
Dawei, Ma.,Geng, Qian,Zhang, Hui,Jiang, Yongwen
supporting information; experimental part, p. 1291 - 1294 (2010/05/17)
(Chemical equation presented) In the pro-line of fire: A general and efficient cascade reaction approach to substituted phenothiazines, which relies on controlled sequential Cul/L-prolinecatalyzed C-S and C-N bond formations, is described. DMSO = dimethylsulfoxide.
Syntheses of the tricyclic cores of clozapine, dibenzo[b,f][1,4]thiazepin- 11(10H)-one, and dibenzo[b,f][1,4]oxazepin-11(10H)-one in C-14 labeled form by [14C]carbonylation
Elmore, Charles S.,Dorff, Peter N.,Richard Heys
, p. 787 - 792 (2013/01/09)
Clozapine has been demonstrated to bind covalently to proteins as a result of metabolic activation that has been proposed to be a precursor to the serious side effects including death that occur in a small percentage of the population. The covalent modifi
