35190-68-2Relevant academic research and scientific papers
Photochemical Oxidation of Pt(IV)Me3(1,2-diimine) Thiolates to Luminescent Pt(IV) Sulfinates
Mala, Barbora,Murtagh, Laura E.,Farrow, Charlotte M. A.,Akien, Geoffrey R.,Halcovich, Nathan R.,Allinson, Sarah L.,Platts, James A.,Coogan, Michael P.
, p. 7031 - 7043 (2021)
We report the formation of dinuclear complexes from, and photochemical oxidation of, (CH3)3-Pt(IV)(N^N) (N^N = 1,2-diimine derivatives) complexes of thiophenolate ligands to the analogous sulfinates (CH3)3Pt(N^N)(SO2Ph) and structural, spectroscopic, and
Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis
Iida, Hiroki,Kozako, Ryo,Oka, Marina
supporting information, p. 1227 - 1230 (2021/06/21)
Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate
Briggs, Edward L.,Tota, Arianna,Colella, Marco,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
, p. 14303 - 14310 (2019/09/06)
Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6-sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles.
Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects
Ajenjo, Javier,Klepetá?ová, Blanka,Greenhall, Martin,Bím, Daniel,Culka, Martin,Rulí?ek, Lubomír,Beier, Petr
supporting information, p. 11375 - 11382 (2019/08/20)
Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.
18F-Fluoroform: A 18F-trifluoromethylating agent for the synthesis of SCF218F-aromatic derivatives
Carbonnel, Elodie,Besset, Tatiana,Poisson, Thomas,Labar, Daniel,Pannecoucke, Xavier,Jubault, Philippe
supporting information, p. 5706 - 5709 (2017/07/10)
Herein the synthesis of various SCF218F-containing derivatives is reported by a transition metal-free process. By using HCF218F, readily generated from a bench-stable difluoromethyl sulfonium salt, various aromatic disulfides were easily converted into the desired radiolabelled trifluoromethylthiolated compounds in the presence of a base. This protocol allowed the formation of the SCF218F-containing aromatic derivatives in good to excellent radiochemical yields. This process was also extended to the corresponding selenium derivative.
Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
supporting information, p. 3477 - 3481 (2016/11/13)
A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
Shedding light on an ultra-bright photoluminescent lamellar gold thiolate coordination polymer [Au(: P -SPhCO2Me)]n
Lavenn, Christophe,Guillou, Nathalie,Monge, Miguel,Podbev?ek, Darjan,Ledoux, Gilles,Fateeva, Alexandra,Demessence, Aude
supporting information, p. 9063 - 9066 (2016/07/21)
The first structure elucidation of a lamellar gold thiolate coordination polymer is described. [Au(p-SPhCO2Me)]n is obtained from the simultaneous esterification of mercaptobenzoic acid and reduction of the Au(iii) precursor. Despite the presence of aurophilic interactions, the intense phosphorescence (QY ～ 70%) originates from intra-ligand and metal-to-ligand transitions.
Haloacid/dimethyl sulfoxide-catalyzed synthesis of symmetrical disulfides by oxidation of thiols
Natarajan, Palani,Sharma, Himani,Kaur, Mandeep,Sharma, Pooja
supporting information, p. 5578 - 5582 (2015/09/21)
A novel method is developed for the oxidation of thiols to the corresponding disulfides using 20 mol % haloacid (HBr or HI) in combination with dimethyl sulfoxide. A tentative mechanism is proposed for the oxidation. In addition to the advantages of cost-effectiveness, simple processes, and broad functional group tolerance, the exclusive formation of disulfides is the principle reward of this methodology while compared to known methods that further oxidize disulfides to S-oxides and other byproducts.
A diphenyl ether derived bidentate secondary phosphine oxide as a preligand for nickel-catalyzed C-S cross-coupling reactions
Wellala, Nadeesha P. N.,Guan, Hairong
, p. 10802 - 10807 (2015/11/17)
A new bidentate secondary phosphine oxide (SPO) was synthesized from diphenyl ether via ortho-lithiation, phosphorylation with PhP(Cl)NEt2, and hydrolysis in an acidic medium. Nickel(0) species ligated with this new SPO was established as a mor
Electrochemical transformation of diazonium salts into diaryl disulfides
Barba, Fructuoso,Ranz, Fernando,Batanero, Belen
experimental part, p. 6798 - 6799 (2010/04/27)
Electrolyses of aryldiazonium tetrafluoroborates in CS2/EtOH and Bu4NClO4, as the solvent-supporting electrolyte system, led to the corresponding diaryl disulfides in good yields.
