60779-24-0Relevant articles and documents
The energy-transfer-enabled biocompatible disulfide–ene reaction
Teders, Michael,Henkel, Christian,Anh?user, Lea,Strieth-Kalthoff, Felix,Gómez-Suárez, Adrián,Kleinmans, Roman,Kahnt, Axel,Rentmeister, Andrea,Guldi, Dirk,Glorius, Frank
, p. 981 - 988 (2018/08/31)
Sulfur-containing molecules participate in many essential biological processes. Of utmost importance is the methylthioether moiety, present in the proteinogenic amino acid methionine and installed in tRNA by radical-S-adenosylmethionine methylthiotransferases. Although the thiol–ene reaction for carbon–sulfur bond formation has found widespread applications in materials or medicinal science, a biocompatible chemo- and regioselective hydrothiolation of unactivated alkenes and alkynes remains elusive. Here, we describe the design of a general chemoselective anti-Markovnikov hydroalkyl/aryl thiolation of alkenes and alkynes—also allowing the biologically important hydromethylthiolation—by triplet–triplet energy transfer activation of disulfides. This fast disulfide–ene reaction shows extraordinary functional group tolerance and biocompatibility. Transient absorption spectroscopy was used to study the sensitization process in detail. The hereby gained mechanistic insights were successfully employed for optimization of the catalytic system. This photosensitized transformation should stimulate bioimaging applications and carbon–sulfur bond-forming late-stage functionalization chemistry, especially in the context of metabolic labelling.
Cleavage of S-S bond by nitric oxide (NO) in the presence of oxygen: A disproportionation reaction of two disulfides
Tsutsumi,Itoh,Ohsawa
, p. 1524 - 1528 (2007/10/03)
Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxygen, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsymmetrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.
Selective thiophilic addition of alkyl- and aryllithiums to dithio esters and a sulfine in the pyridine series
Lempereur, Claude,Plé, Nelly,Truck, Alain,Quéguiner, Guy,Corbin, Florence,Alayrac, Carole,Metzner, Patrick
, p. 2019 - 2034 (2007/10/03)
Reaction of two dithio esters and a new sulfine (S-thiocarbonyl oxide) with various aryl- and alkyllithiums at -78°C afforded dithio acetals or their oxides, arising from a thiophilic addition. The intermediate carbanions can be trapped by alkyl halides or an aldehyde. This provides a new entry to pyridyl acyl anions, "Umpolung" synthons.
