57642-62-3Relevant 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.
Nickel-catalyzed cycloadditions of thiophthalic anhydrideswith alkynes
Inami, Tasuku,Baba, Yoko,Kurahashi, Takuya,Matsubara, Seijiro
supporting information; experimental part, p. 1912 - 1915 (2011/06/22)
Nickel-catalyzed cycloadditions have been developed where thiophthalic anhydrides reactwith alkynes to afford substituted sulfur-containing heterocyclic compounds. Selective formations of thioisocoumarins, benzothiophenes, and thiochromoneswre accomplishe
Novel syntheses of 2,3-disubstituted benzothiophenes
Katritzky,Kirichenko,Ji, Yu,Prakash
, p. 156 - 164 (2007/10/03)
The sodium salts of o-sulfanylphenyl ketones 3a-g were treated with α-benzotriazol-1-ylalkyl chlorides 4a,b to give intermediates 5a-k in good yields. Compounds 5a-k, on treatment successively with LDA and Ti (0), gave benzothiophenes 7a-k.
