5459-63-2Relevant academic research and scientific papers
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.
Sequential C-H activation enabled expedient delivery of polyfunctional arenes
Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
supporting information, p. 8075 - 8078 (2021/08/20)
Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
A novel pathway for the thermolysis of N-nitrosoanthranilates using flash vacuum pyrolysis leading to 7-aminophthalides
Dallinger, Doris,Kappe, C. Oliver,Zlatkovi?, Dragan
supporting information, p. 8371 - 8375 (2020/11/05)
Flash vacuum pyrolysis of methyl N-methyl-N-nitrosoanthranilate leads to elimination of nitric oxide and disproportionation of the formed N-radical to 7-(methylamino)phthalide and methyl N-methylanthranilate. This transformation was found to be a convenient, solvent-free method for the preparation of 7-(methylamino)phthalides. An alternative route through pyrolysis of N-benzyl-N-methyl anthranilates was also investigated. This journal is
Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
supporting information, p. 1432 - 1438 (2019/03/26)
The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid
Benoit, Emeline,Fnaiche, Ahmed,Gagnon, Alexandre
, p. 1162 - 1171 (2019/06/08)
The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.
Reusable cobalt-phthalocyanine in water: Efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds
Dou, Yingchao,Huang, Xin,Wang, Hao,Yang, Liting,Li, Heng,Yuan, Bingxin,Yang, Guanyu
supporting information, p. 2491 - 2495 (2017/07/17)
A new aerobic oxidative coupling of thiols in water to construct sulfenamides or disulfides was developed, utilizing cobalt(ii)phthalocyanine-tetra-sodium sulfonate as the catalyst and O2 as the oxidant. The mother liquor could be recycled up to 20 times with negligible loss of activity and only a minor decrease of product yield.
Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides
Viani, Fiorenza,Rossi, Bianca,Panzeri, Walter,Merlini, Luca,Martorana, Alessandra M.,Polissi, Alessandra,Galante, Yves M.
, p. 1745 - 1761 (2017/03/08)
1,2-Benzisothiazol-3(2H)-one (BIT) is one of the most common chemical biocides in industrial products, with a heterocyclic structure and a wide range of antimicrobial activity. A library of BIT derivatives was synthesized and characterized, from which 18 compounds were selected, tested for anti-bacterial activity relative to the parent molecule and amenable of coupling to plant polysaccharides in general and to galactomannans (GM) in particular, widely used as rheology modifiers, but with limited “biostability”. Four sites on the BIT core were targeted: the nitrogen and the oxygen atoms on the heterocyclic ring, the C5 and the C6 positions on the aromatic ring, where functional groups were introduced. The ultimate aim of this work is to establish whether by covalently linking a biocide to GM polymers, their “biostability” can be improved.
Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
supporting information, p. 903 - 909 (2017/06/23)
A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
supporting information, p. 2808 - 2811 (2016/07/06)
A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
SNAr nucleophilic substitution of 1,9-dihalodipyrrins by S- and N- nucleophiles. Synthesis of new dipyrrins bearing pendant substituents
Leushina, Evgenia,Tikhomirova, Ksenia,Permyakova, Anastasiya,Ilin, Pavel,Terenina, Maria,Anisimov, Alexander,Khoroshutin, Andrey
, p. 149 - 155 (2016/03/19)
5-Aryl-1,9-dichlorodipyrrins react with a series of S- and N- nucleophiles (both alkyl- and aryl- ones). Reagents with mercapto group yield product of double nucleophilic substitution of 5-pheny-1,9-dichlorodipyrrin, i.e. the respective 1,9-bis(alkyl-of arylthio)dipyrrin. On the contrary, 5-(4-nitrophenyl)-1,9-dichlorodipyrrin causes disulfides formation from the S-aliphatic substrates, whereas nucleophilic substitution remains the main path of the reaction for S-aryl ones. The reaction of N-Alkyl nucleophiles proceeds as mono-substitution. UV-Vis spectra feature a batochromic shift for bis-S-substituted products and a hypsochromic shift for mono-N-substituted ones, with respect to the starting dichlrorides.
