799764-32-2Relevant academic research and scientific papers
Aerobic Cross-Dehydrogenative Coupling Reactions for Selective Mono- And Dithiolation of Phenols
Han, Dong-Yang,Liu, Xiao-Peng,Li, Ruo-Pu,Xu, Da-Zhen
, p. 10166 - 10176 (2021/07/31)
A highly efficient strategy for the direct thiolation of phenols under transition metal-free and solvent-free conditions has been developed. These reactions are operationally simple with employing air (molecular oxygen) as an ideal oxidant and can selectively provide mono- and dithiolation products in good to excellent yields under basic conditions. The reaction tolerates a broad range of aryl thiols and arenes and is especially applicable for large-scale synthesis.
Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis
Chen, Bin,Chen, Ya-Jing,Cheng, Yuan-Yuan,Lei, Tao,Liang, Ge,Tung, Chen-Ho,Wang, Jing-Hao,Wu, Li-Zhu,Ye, Chen,Zhou, Chao
supporting information, p. 8082 - 8087 (2021/10/25)
An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide
Chalcogenylation of Naphthalene Derivatives Catalyzed by Iron(III) Chloride and Potassium Iodide
Seckler, Diego,Da Luz, Eduardo Q. Da,Silvério, Gabriel L.,Badshah, Gul,Lima, David B.,Abreu, Emerson A.,Albach, Breidi,Ribeiro, Ronny R.,Rampon, Daniel S.
supporting information, p. 940 - 946 (2021/04/15)
We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl 3and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2
Metal- And solvent-free direct C-H thiolation of aromatic compounds with sulfonyl chlorides
Zhao, Feng,Tan, Qi,Wang, Dahan,Deng, Guo-Jun
supporting information, p. 427 - 432 (2020/02/13)
A simple, efficient and green method for the direct thiolation of aromatic compounds using commercially available sulfonyl chlorides as the sulfur source was developed under metal- and solvent-free conditions. The C-S bond was constructed via direct C-H functionalization of diverse aromatic compounds under an oxygen atmosphere. In this process, various diaryl sulfides were synthesized in moderate to excellent yields. This protocol shows a broad substrate scope and good functional group tolerance. Moreover, a gram-scale experiment was also conducted to prove the prospect of this method for the scale-up synthesis of diaryl sulfides. Mechanistic studies indicate that this procedure probably undergoes a radical pathway.
CuI-catalyzed direct synthesis of diaryl thioethers from aryl boronic acids and arylsulfonyl chlorides
Huang, Keke,Yang, Min,Lai, Xiao-Jing,Hu, Xin,Qiu, Guanyinsheng,Liu, Jin-Biao
, (2019/12/27)
A CuI-catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed. The reaction is initiated by a PPh3 reduction of the arylsulfonyl chloride, followed by a CuI-catalyzed C–S coupling with an aryl boronic acid. Various arylsulfonyl chlorides can directly serve as a sulfur source in this mild and efficient reaction giving the desired products in moderate to good yields. Moreover, this practical method has also been applied to the thioetherification of aryl iodides and acetylacetones.
Regioselective Ortho‐C–H sulfenylation of free phenols catalyzed by Co(II)-immobilized on silica-coated magnetic nanoparticles
Khaef, Sepideh,Rostami, Abed,Khakyzadeh, Vahid,Zolfigol, Mohammad Ali,Taherpour, Avat Arman,Yarie, Meysam
, (2020/01/22)
Fe3O4?SiO2-UT?CoII is prepared by the silica-coated magnetic nanoparticles, urea-triazole, and CoCl2. This organic-inorganic hybride composite showed a good to excellent catalytic activity toward regioselective ortho-sulfenylation of free phenols and naphthols using pivalic anhydride as a directing group, also K2S2O8 and PPh3 were employed as oxidant and additive respectively. The newly synthesized catalyst was fully characterized by using different techniques such as FT-IR, TGA, DTG, TEM, SEM, EDS, ICP and VSM analyses. The competitive price, accessibility and lower toxicity of cobalt compared to expensive transition metals using for C–H bond activation and functionalization constitute precious advantages for this method. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its catalytic activity after five cycles.
TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME
Jie, Zhang,Jing, He,Ping, Liu,Xuezhen, Li,Yali, Liu,Yueting, Wei
supporting information, (2020/10/13)
An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.
Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
, p. 2660 - 2675 (2019/03/14)
Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
Metal free, facile sulfenylation of ketene dithioacetals catalyzed by an HBr-DMSO system
Sorabad, Ganesh Shivayogappa,Maddani, Mahagundappa Rachappa
supporting information, p. 5996 - 6000 (2019/04/16)
A transition metal free, highly efficient, sulfenylation of ketene dithioacetals catalyzed by an HBr-DMSO system is achieved. This strategy employs inexpensive and readily available HBr and DMSO to provide a direct C-H bond sulfenylation with a broad rang
Lewis Base/Bronsted Acid Dual-Catalytic C-H Sulfenylation of Aromatics
Nalbandian, Christopher J.,Brown, Zachary E.,Alvarez, Erik,Gustafson, Jeffrey L.
supporting information, p. 3211 - 3214 (2018/06/11)
A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.
