94404-28-1Relevant academic research and scientific papers
Switchable Synthesis of Sulfoxides and α-Alkoxy-β-ketothioethers Regulated by Temperature in a Selectfluor-Methanol System
Wang, Jiateng,Liu, Mengxia,Zhang, Yue,Bi, Gehua,Zhao, Yi,Yang, Kai,Huang, Xin
, p. 14404 - 14419 (2021/11/01)
A switchable and benign protocol for chemoselective synthesis of sulfoxides and α-alkoxy-β-ketothioethers has been developed. It was determined that various thiophenols and alkenes/alkynes are compatible to realize the target compounds from a medium to a high yield by regulating the reaction temperature. In particular, methanol not only served as a solvent but also participated in the reaction process as a hydrogen donor. In this study, Selectfluor has been proved to be an efficient multifunctional reagent in the reaction system.
Visible-light-activated selective synthesis of sulfoxides via thiol-ene/oxidation reaction cascade
Singh, Manjula,Yadav, Arvind K.,Yadav, Lal Dhar S.,Singh
, p. 450 - 453 (2018/01/05)
A convenient, highly selective and metal-free synthesis of sulfoxides from alkenes and thiols using NHPI as an inexpensive and reusable organophotoredox catalyst is reported. The protocol involves radical thiol-ene/oxidation reaction cascade and utilizes visible light and air (O2) as inexpensive, readily available, non-toxic and eco-sustainable reagents to afford up to 96% yields of the product at room temperature.
Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant
Cui, Huanhuan,Wei, Wei,Yang, Daoshan,Zhang, Yulong,Zhao, Huijuan,Wang, Leilei,Wang, Hua
supporting information, p. 3520 - 3524 (2017/08/15)
A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.
Thiol-ene/oxidation tandem reaction under visible light photocatalysis: Synthesis of alkyl sulfoxides
Guerrero-Corella, Andrea,María Martinez-Gualda, Ana,Ahmadi, Fereshteh,Ming, Enrique,Fraile, Alberto,Alemán, José
supporting information, p. 10463 - 10466 (2017/09/25)
The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results.
Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides
Yue, Hui-Lan,Klussmann, Martin
supporting information, p. 2505 - 2509 (2016/10/24)
An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.
Palladium(II)-catalyzed ortho -olefination of arenes applying sulfoxides as remote directing groups
Wang, Binjie,Shen, Chuang,Yao, Jinzhong,Yin, Hong,Zhang, Yuhong
supporting information, p. 46 - 49 (2014/01/23)
A novel palladium-catalyzed ortho-C(sp2)-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.
Synthesis of sulfur-bridged polycycles via Pd-catalyzed dehydrogenative cyclization
Wang, Binjie,Liu, Yue,Lin, Cong,Xu, Yiming,Liu, Zhanxiang,Zhang, Yuhong
supporting information, p. 4574 - 4577 (2015/01/08)
A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp2)-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.
Pyrolysis of Sulfoxide Bearing Electron-Withdrawing Substituents on β-Position in S-Ethyl Group of Ethyl Phenyl Sulfoxide
Yoshimura, Toshiaki,Yoshizawa, Masaki,Tsukurimichi, Eiichi
, p. 2491 - 2496 (2007/10/02)
In order to obtain information concerning the reaction mechanism of the pyrolysis of a sulfoxide bearing an electron-withdrawing substituent on the β-position in the S-ethyl group of ethyl phenyl sulfoxide, 2-(substituted phenyl)ethyl aryl sulfoxides (1) and 2-cyanoethyl (substituted phenyl)sulfoxides (2) were pyrolyzed.The rate-enhancing effect of the β-phenyl group of 1 was small.The activation enthalpy and entropy of 1 were found to be 110 kJ mol-1 and -45 JK-1mol-1, respectively.Hammett plots for 1 gave positive trends for the substituents, both on the β-phenyl group (ρ=0.76) and on the S-phenyl group (ρ=0.32), though the ρ-value of the latter was about half of the former.On the other hand, the Hammett plot for 2 did not give a straight line, but a concave curve in which a series of substituents from the p-OCH3 to p-Cl groups gave a negative trend (ρ=-0.49), while the p-NO2 group afforded a positive trend.The pyrolytic rate of 2 was found to be about 23-times faster than that of 1 at 100 deg C.The kinetic isotope effect for β-position hydrogen in the β-phenylethyl group of 1 was considerably large (kH/kD=4.3).From the obtained results, it was suggested that the pyrolysis of 1 and 2 proceeds via a nearly carbanion-like mechanism in a five-membered cyclic transition state.
