69446-60-2Relevant academic research and scientific papers
Two-Step Synthesis of Unsymmetrical Diaryl Sulfides by Electrophilic Thiolation of Non-functionalized (Hetero)arenes
B?hm, Marvin J.,Golz, Christopher,Rüter, Isabelle,Alcarazo, Manuel
, p. 15026 - 15035 (2018/09/25)
This article reports the efficient preparation of a series of unsymmetrically substituted thioethers through a two-step procedure consisting of an initial metal-free C?H sulfenylation of electron-rich (hetero)arenes with newly prepared succinylthioimidazolium salts. Subsequent reaction of the arylthioimidazolium intermediates with Grignard reagents afford the desired thioethers. The synthetic protocol described is modular, scalable, and high yielding, and provides access to sulfides that are not easy to obtain through the existing methodologies. Importantly, no prefunctionalization of the initial (hetero)arene is required.
Sodium Iodide (NaI)-Catalyzed Cross-Coupling for C?S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides
Wang, Hui-Hong,Shi, Tao,Gao, Wei-Wei,Wang, Yong-Qiang,Li, Jun-Fang,Jiang, Yi,Hou, Yong Sheng,Chen, Chen,Peng, Xue,Wang, Zhen
supporting information, p. 2675 - 2679 (2017/10/18)
A simple and practical NaI-catalyzed direct C?H sulfenylation of arenes has been developed under air. In this reaction, aryl sulfides were obtained in moderate to excellent yields with high regioselectivity from readily available aromatic compounds and aryl/alkyl thiols, even on gram scale. To demonstrate the practicability of this reaction, two bioactive compound skeletons were synthesized in good yields. This method can also be used to late-stage modification of curcumin.
DMSO/iodine-catalyzed oxidative C-Se/C-S bond formation: A regioselective synthesis of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes
Saba, Sumbal,Rafique, Jamal,Braga, Antonio L.
, p. 3087 - 3098 (2016/05/24)
A convenient metal-free and solvent-free iodine-catalyzed regioselective greener protocol to access different types of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes through oxidative C-Se/C-S formation via direct C(sp2)-H bond activation was developed. The products were obtained in good to excellent yields using [O or N]-containing arenes, half equiv. of various odorless diorganyl dichalcogenides (S/Se), iodine (20 mol%) as the catalyst and 3 equiv. of DMSO as the oxidant, applying MW irradiation for 10 min.
Iodine-Mediated Synthesis of Aromatic Thioethers with Aromatic Amines and Sulfonyl Hydrazides in High Regioselectivity via C(sp2)-H Bond Functionalization
Pang, Xiaobo,Xiang, Likui,Yang, Xiaodong,Yan, Rulong
supporting information, p. 321 - 325 (2016/02/14)
An iodine-mediated synthesis of aromatic thioethers from aromatic amines and sulfonyl hydrazides via C(sp2)-H bond functionalization and C-S bond formation has been developed. In this procedure, various substituents on the sulfonyl hydrazides, such as alkyl, methoxyl, chloro, bromo and fluoro groups, and aromatic amines are tolerated in the thiolation which generates the desired products in moderate to good yields.
Iodine-mediated thiolation of phenol/phenylamine derivatives and sodium arylsulfinates in neat water
Wang, Dingyi,Zhang, Rongxing,Lin, Sen,Yan, Zhaohua,Guo, Shengmei
, p. 108030 - 108033 (2016/01/09)
An efficient and convenient protocol for iodine-mediated thiolation of phenols/phenylamines with sodium benzene-sulfinates in water has been achieved. In this transformation, environment-friendly conditions (including metal-free and water as solvent) are employed under air conditions, and a series of valuable thioethers are easily obtained in moderate to good yields.
