21948-75-4Relevant articles and documents
Nitrite increases the enantioselectivity of sulfoxidation catalyzed by myoglobin derivatives in the presence of hydrogen peroxide
Pironti, Vincenza,Nicolis, Stefania,Monzani, Enrico,Colonna, Stefano,Casella, Luigi
, p. 8153 - 8160 (2004)
The effect of nitrite in the sulfoxidation of organic sulfides catalyzed by myoglobin (Mb) in the presence of hydrogen peroxide has been investigated. A general improvement in enantioselectivity was found for the reaction catalyzed by horse heart metMb and a series of sperm whale metMb derivatives including the wild type protein, the active site mutants T67K Mb, T67R Mb, T67R/S92D Mb, and the T67K Mb derivative reconstituted with the modified prosthetic group protohemin-l- histidine methyl ester. Graphical Abstract
Accelerated Oxidation of Organic Sulfides by Microdroplet Chemistry
Li, Jia,Liu, Chengyuan,Chen, Hao,Zare, Richard N.
, p. 5011 - 5015 (2021/04/02)
We report the rapid oxidation of organic sulfides to sulfoxides by means of microdroplet chemistry at room temperature using a spray solution containing an organic sulfide dissolved in water/methanol, dilute (11%-14%) sodium hypochlorite (NaClO), and 5% chloroauric acid (HAuCl4). Ultrasonic nebulization, easy ambient sonic-spray ionization, or electrosonic spray ionization serves as the microdroplet source. High-resolution mass spectrometry was used as an online detector, and nuclear magnetic resonance was used as an offline detector. We found that the sulfoxide yields vary between 66 and 95%, the highest rate of product formation is 195 mg/min for benzyl phenyl sulfoxide, and the time required is a few minutes, which is much less than that required for the conventional means of achieving this chemical transformation. We also applied this microdroplet method to protein fingerprinting. We found that protein sequences containing methionine can be quickly oxidized, providing useful information for protein structure determinations.
Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones
Li, Jin-Heng,Li, Yang,Sun, Qing,Xue, Qi,Zhang, Ting-Ting
supporting information, p. 10314 - 10318 (2021/12/17)
A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is
Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
Amri, Nasser,Wirth, Thomas
, p. 15961 - 15972 (2021/07/20)
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
