67284-17-7Relevant academic research and scientific papers
Copper-assisted preparation of pyridinyl sulfonate esters from hydroxypyridines and sodium sulfinates
Fan, Qiangwen,Le, Zhang-Gao,Li, Qian,Liu, Yishuai,Xie, Zongbo,Yang, Liu,Zhu, Haibo
, p. 2736 - 2740 (2022/02/09)
An efficient and powerful copper-assisted method for the effective conversion of a broad range of hydroxypyridines and sodium sulfinates into their corresponding pyridinyl tosylates was developed. Key features of this base- and ligand-free protocol include using the cheap and readily available CuBr2 as a medium and the use of sodium sulfinates as formal sulfonylation reagents. A variety of functional pyridinyl tosylates could be formed with good yields, which can easily be converted into C-C and C-N bond-containing compounds. This journal is
Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective
Gui, Yong-Yuan,Liao, Li-Li,Sun, Liang,Zhang, Zhen,Ye, Jian-Heng,Shen, Guo,Lu, Zhi-Peng,Zhou, Wen-Jun,Yu, Da-Gang
supporting information, p. 1192 - 1195 (2017/02/05)
Herein is reported the mild and general coupling of amine/ether C(sp3)-H bonds with various kinds of C(sp2)-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (>50 examples), good functional group tolerance and facile product modification.
Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates
Yi, Zubaoyi,Aschenaki, Yodit,Daley, Ryan,Davick, Stephen,Schnaith, Abigail,Wander, Rylee,Kalyani, Dipannita
, p. 6946 - 6957 (2017/07/13)
Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenz
A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution
Kassanova, Assiya Zh.,Krasnokutskaya, Elena A.,Beisembai, Perizat S.,Filimonov, Victor D.
, p. 256 - 262 (2016/01/15)
The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid.
Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
Lei, Xiangyang,Jalla, Anusha,Abou Shama, Mhd A.,Stafford, Jamie M.,Cao, Billy
supporting information, p. 2578 - 2585 (2015/09/01)
Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding
Iron-catalyzed cross-coupling reactions of alkyl grignards with aryl sulfamates and tosylates
Agrawal, Toolika,Cook, Silas P.
supporting information, p. 96 - 99 (2013/03/28)
The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and β-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF3·3H2O was critical to minimize nucleophile isomerization.
A new one-pot solvent-free synthesis of pyridinyl tosylates via diazotization of aminopyridines
Tretyakov, Alexey N.,Krasnokutskaya, Elena A.,Gorlushko, Dmitry A.,Ogorodnikov, Vladimir D.,Filimonov, Victor D.
supporting information; experimental part, p. 85 - 87 (2011/02/25)
A new, convenient, one-pot method for the synthesis of pyridinyl tosylates is developed. The procedure involves sequential diazotization/tosylation of aminopyridines with sodium nitrite and p-toluenesulfonic acid under solvent-free conditions in a water p
N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates
Kuroda, Jun-Ichi,Inamoto, Kiyofumi,Hiroya, Kou,Doi, Takayuki
experimental part, p. 2251 - 2261 (2009/08/09)
Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).
Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature
Ogata, Tokutaro,Hartwig, John F.
supporting information; experimental part, p. 13848 - 13849 (2009/02/07)
Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright
Palladium-catalyzed carbonylation of aryl tosylates and mesylates
Munday, Rachel H.,Martinelli, Joseph R.,Buchwald, Stephen L.
, p. 2754 - 2755 (2008/09/19)
A general protocol for the palladium-catalyzed carbonylation of aryl tosylates and mesylates to form esters has been developed using a catalyst system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand. The system operates under mild conditions: atmospheric CO pressure and temperatures of 80-110 °C. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance. Copyright
