71778-40-0Relevant articles and documents
Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst
Pramanik, Milan,Choudhuri, Khokan,Mathuri, Ashis,Mal, Prasenjit
supporting information, p. 10211 - 10214 (2020/09/21)
We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as a terminal oxidant. EPR analysis and Stern-Volmer
A Transition-Metal-Free and Base-Mediated Carbene Insertion into Sulfur-Sulfur and Selenium-Selenium Bonds: An Easy Access to Thio- and Selenoacetals
Arunprasath, Dhanarajan,Sekar, Govindasamy
, p. 698 - 708 (2017/02/23)
A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol-free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated. (Figure presented.).
Ethyl lactate mediated thioacetalization of aldehydes at ambient temperature
Wan, Jie-Ping,Jing, Yanfeng,Liu, Yunyun
, p. 1302 - 1305 (2016/09/28)
Dithioacetalization reactions of aldehydes with thiols/thiophenols have been successfully achieved at room temperature by employing the green, bio-based ethyl lactate as the reaction medium. By means of this sustainable approach, a class of dithioacetals has been acquired with high diversity and efficiency.
Rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles with disulfides: An entry to diverse transformation of terminal alkynes
Zhang, Hao,Wang, Hui,Yang, Haijun,Fu, Hua
, p. 6149 - 6153 (2015/06/08)
An efficient and useful rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles has been developed for the first time. The protocol uses readily available N-sulfonyl-1,2,3-triazoles and diaryl disulfides as the starting materials. The corresponding hydrolytic and reductive products with thioacetals were obtained in good to excellent yields, and the reactions were carried out easily under mild conditions with tolerance of some functional groups. Furthermore, the generated thioacetals could be transformed into some useful compounds. Therefore, the present method provides a novel and valuable strategy for the diverse transformation of alkynes.
Mesoporous silica-functionalized dual Br?nsted acidic ionic liquid as an efficient catalyst for thioacetalization of carbonyl compounds in water
Vafaeezadeh, Majid,Dizicheh, Zahra Bahrami,Hashemi, Mohammad Mahmoodi
, p. 96 - 100 (2013/09/02)
A novel silica-functionalized dual Br?nsted acidic ionic liquid (ionic liquid with two Br?nsted acidic species) has been reported as a highly efficient catalyst for thioacetalization of carbonyl compounds. The reaction was efficiently performed in water a
Green, catalyst-free thioacetalization of carbonyl compounds using glycerol as recyclable solvent
Perin, Gelson,Mello, Luzia G.,Radatz, Cátia S.,Savegnago, Lucielli,Alves, Diego,Jacob, Raquel G.,Lenard?o, Eder J.
experimental part, p. 4354 - 4356 (2010/09/12)
We describe herein the use of glycerol as an efficient and a recyclable solvent in the thioacetalization of aldehydes and ketones. The catalyst-free reactions proceed easily using glycerol at 90 °C and the corresponding thioacetals were obtained in good to excellent yields. Glycerol was recovered and utilized for further thioacetalization reactions.
Cerium triflate: An efficient and recyclable catalyst for chemoselective thioacetalization of carbonyl compounds under solvent-free conditions
Kumar, Anil,Rao, M. Sudershan,Kameshwara Rao
experimental part, p. 135 - 140 (2010/05/18)
A simple and efficient chemoselective thioacetalization of carbonyl compounds has been achieved using Ce(OTf)3 (10 mol-%) as a catalyst under solvent-free conditions. Advantages of the methodology include very short reaction times, excellent yi
A mild method for the protection of aldehydes as dithioacetals and dithiolanes catalyzed by I2 generated in situ using Fe(NO 3)3.9H2O/Nai under heterogeneous conditions
Rostami, Amin,Nik, Heidar Ali Alavi,Roosta, Zahra Toodeh,Khazaei, Ardeshir
experimental part, p. 431 - 434 (2009/12/03)
Structurally diverse aromatic aldehydes were thioacetalated in a clean and efficient reaction with ethane-1,2-dithiol and thiophenol based on the use of I2 generated in situ from Fe(NO3)3.9H 2O/NaI. The reaction occurs in good to high yield in dichloromethane at room temperature and the use of toxic and corrosive molecular iodine is avoided.
Nucleophilic fluoroalkylation of α,β-enones, arynes, and activated alkynes with fluorinated sulfones: Probing the hard/soft nature of fluorinated carbanions
Ni, Chuanfa,Zhang, Laijun,Hu, Jinbo
, p. 5699 - 5713 (2008/12/21)
(Chemical Equation Presented) We have successfully accomplished the nucleophilic fluoroalkylation of α,β-enones, arynes, and activated alkynes with fluorinated sulfones. It was found that for acylic α,β-enones, although the reaction medium and the structure of the enones can all influence the regioselectivity of the nucleophilic alkylation reactions, the hard/soft nature of the carbanions played a major role. By using the 1,4- and 1,2-addition product ratio as a probe to determine the hard/soft nature of the above-mentioned four halogenated carbanions, the order of the softness of these carbanions can be given as follows: [(PhSO2) 2CF-] (20) ≈ PhSO2CCl2 - (32) > PhSO2CHF- (31) > PhSO 2CF2- (30). In the case of fluoroalkylation of aryne (35 as the precursor) and α,β-acetylenic ketones 46 with fluorobis(phenylsulfonyl)methane (21), fluorobis(phenylsulfonyl)methylated arenes 36 and β-fluorobis(phenylsulfonyl)methylated α,β-enones 47 were obtained as the corresponding products in good yields. During the reaction between 2-fluoro-2-(phenylsulfonyl)acetophenone (34) and arynes or activated alkynes 46, an intramolecular tandem reaction process leads to the formation of acyl-fluoroalkylated arenes 43 or α-acyl-β- fluoroalkylated α,β-enones 48. It turned out that the softness of a fluorine-bearing carbanion (such as 20 or 33 derived from 21 or 34) plays a crucial role for the success of the nucleophilic fluoroalkylation reactions with arynes and some activated alkynes (α,β-acetylenic ketones).
Design and synthesis of (E)-1,1,2-triarylethenes: Novel inhibitors of the cyclooxygenase-2 (COX-2) isozyme
Uddin, Md. Jashim,Rao, P.N. Praveen,McDonald, Robert,Knaus, Edward E.
, p. 439 - 442 (2007/10/03)
A novel class of acyclic 1,1,2-triaryl (E)-ethenes was designed that were synthesized via an (E)-selective Takeda olefination reaction. Among the group of compounds evaluated, (E)-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)-1- phenylethene (10c) emerged as the most potent (COX-2 IC50 = 0.0316 μM), and selective (selectivity index > 3164), COX-2 inhibitor.
