6099-23-6Relevant articles and documents
Photoredox-Mediated Synthesis of Functionalized Sulfoxides from Terminal Alkynes
Kumar, Jaswant,Ahmad, Ajaz,Rizvi, Masood Ahmad,Ganie, Majid Ahmed,Khajuria, Chhavi,Shah, Bhahwal Ali
supporting information, p. 5661 - 5665 (2020/07/14)
A photoredox-mediated protocol for the synthesis of α-alkoxy-β-ketosulfoxides and α,β-dialkoxysulfoxides using alkynes, thiol, and alcohols is reported. This work presents a rare single-step synthesis of α-substituted sulfoxides, involving tandem introduction of a thiol and alcohol as a key enabling advancement. Furthermore, the method can be easily employed to access vinyl sulfoxides and β-ketosulfoxides.
Stereochemical analysis of β-keto sulfoxides by circular dichroism
Górecki, Marcin,Capozzi, Maria Annunziata M.,Albano, Gianluigi,Cardellicchio, Cosimo,Di Bari, Lorenzo,Pescitelli, Gennaro
, p. 29 - 42 (2017/11/13)
Three β-keto sulfoxides (1–3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, t
One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents
Fakhry, Jerome,Grayson, David H.
, p. 556 - 563 (2017/12/28)
Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.
A route to benzylic arylsulfoxides from β-ketosulfoxides
Chang, Meng-Yang,Cheng, Yu-Chieh,Chan, Chieh-Kai
, p. 4068 - 4075 (2016/07/06)
The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.
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.
Polymeric ionic liquid nanogel-anchored tungstate anions: A robust catalytic system for oxidation of sulfides to sulfoxides
Pourjavadi, Ali,Nazari-Chamazkoti, Mojtaba,Hosseini, Seyed Hassan
, p. 1348 - 1354 (2015/02/19)
A new heterogeneous catalytic system was prepared by immobilization of tungstate ions on a cross-linked poly(ionic liquid) nanogel. The solid nanogel was easily synthesized by a surfactant-less method. The resulting catalyst was highly active in selective
Visible light organophotoredox catalysis: A general approach to β-keto sulfoxidation of alkenes
Keshari, Twinkle,Yadav, Vinod K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
, p. 3986 - 3992 (2014/08/05)
A mild, simple, efficient and metal-free approach to β-keto sulfoxides utilising eosin Y as an organophotoredox catalyst has been developed. This general protocol offers a direct and rapid difunctionalization of alkenes using thiophenols and atmospheric oxygen at room temperature in a one-pot procedure. The utilisation of visible light and air (O2) as inexpensive, readily available, non-toxic and eco-sustainable reagents makes this protocol compatible with the green chemistry demands. This journal is the Partner Organisations 2014.
Photofunctional Eu3+/Tb3+ hybrids through sulfoxide linkages: Coordination bonds construction, characterization and luminescence
Guo, Lei,Yan, Bing,Liu, Jin-Liang
, p. 4933 - 4940 (2011/06/27)
New kinds of organic-inorganic hybrid materials consisting of rare earth (Eu3+, Tb3+) complexes covalently bonded to a silica-based network have been obtained by a sol-gel approach. Three novel versatile molecular building blocks con
Oxidation of sulfides with N-bromosuccinimide in the presence of hydrated silica gel
Ali, Mohammed Hashmat,Hartman, Melanie,Lamp, Kimberly,Schmitz, Chad,Wencewicz, Tim
, p. 1769 - 1777 (2007/10/03)
An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N-bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermed
First synthesis of β-keto sulfoxides by a palladium-catalyzed carbonylative suzuki reaction
Medio-Simon, Mercedes,Mollar, Cristian,Rodriguez, Nuria,Asensio, Gregorio
, p. 4669 - 4672 (2007/10/03)
(Chemical Equation Presented) An unprecedented palladium-catalyzed three-component cross-coupling reaction between α-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of β-ketosulfoxides. T
