32884-77-8Relevant academic research and scientific papers
Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
Xiang, Haonan,Liu, Jie,Wang, Jieping,Jiang, Lvqi,Yi, Wenbin
supporting information, p. 181 - 185 (2021/12/17)
A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barr
Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PIII/PV=O Redox Cycling
Ghosh, Avipsa,Lecomte, Morgan,Kim-Lee, Shin-Ho,Radosevich, Alexander T.
supporting information, p. 2864 - 2869 (2019/02/01)
A method for electrophilic sulfenylation by organophosphorus-catalyzed deoxygenative O-atom transfer from sulfonyl chlorides is reported. This C?S bond-forming reaction is catalyzed by a readily available small-ring phosphine (phosphetane) in conjunction with a hydrosilane terminal reductant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfluoroalkyl, and heteroaryl derivatives that are otherwise difficult to access. Mechanistic investigations indicate that the twofold deoxygenation of the sulfonyl substrate proceeds by the intervention of an off-cycle resting state thiophosphonium ion. The catalytic method represents an operationally simple protocol using a stable phosphine oxide as a precatalyst and exhibits broad functional-group tolerance.
Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
Matsugi,Murata,Gotanda,Nambu,Anilkumar,Matsumoto,Kita
, p. 2434 - 2441 (2007/10/03)
A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
An efficient sulfenylation of aromatics using highly active quinone mono O,S-acetal bearing a pentafluorophenylthio group
Matsugi, Masato,Murata, Kenji,Nambu, Hisanori,Kita, Yasuyuki
, p. 1077 - 1080 (2007/10/03)
A facile sulfenylation of various aromatic nuclei was achieved by use of the novel sulfenylation reagent, the quinone mono O,S-acetal bearing a pentafluorophenylthio group. It functioned below 0°C in the presence of a catalytic amount of TMSOTf.
