7598-28-9Relevant academic research and scientific papers
Tosylation of endocrine-disruptive alkylphenolic compounds in a solid-phase reaction system consisting of C18-modified silica gel and aqueous buffer solution
Uno, Bunji,Okumura, Noriko
, p. 1470 - 1472 (2004)
The tosylation reaction of endocrine-disruptive alkylphenolic compounds in a solid-phase aqueous system was investigated with the aim of developing an environment-friendly and efficient derivatization method for HPLC analyses of environmental samples. The
Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates
Pospech, Jola,Taeufer, Tobias
, p. 7097 - 7111 (2020/06/27)
This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.
Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage
Zhang, Liangwei,Liu, Long,Huang, Tianzeng,Dong, Qizhi,Chen, Tieqiao,Chen, Tieqiao
, p. 2189 - 2196 (2020/06/05)
A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t
Synthesis and DFT studies of novel aryloxymaleimides via nucleophilic substitution of tosyloxy group
Yan, Maocai,Zhang, Zhen,Zhou, Jinhui,Li, Wei,Zhang, Chunyan,Zhang, Jingchang,Wang, Huannan,Yang, Xuelu,Fan, Shuai,Yang, Zhaoyong
, p. 155 - 160 (2019/04/26)
Maleimide skeleton distributes widely in a great many substances, and maleimides are very useful building blocks in organic synthesis and many related disciplines, like bioconjugation. As an excellent leaving group, tosyloxy (-OTs) group are very popular
Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates
Huang, He,Wu, Yang,Zhang, Wen,Feng, Chun,Wang, Bi-Qin,Cai, Wan-Fei,Hu, Ping,Zhao, Ke-Qing,Xiang, Shi-Kai
, p. 3094 - 3101 (2017/03/23)
Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.
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
Aryl tosylates as non-ionic photoacid generators (PAGs): Photochemistry and applications in cationic photopolymerizations
Torti, Edoardo,Della Giustina, Gioia,Protti, Stefano,Merli, Daniele,Brusatin, Giovanna,Fagnoni, Maurizio
, p. 33239 - 33248 (2015/04/27)
The irradiation of various substituted aryl tosylates was investigated in a solution and homolysis of the ArO-SO2C6H4CH3 bond was the path exclusively observed. The corresponding phenols and photo-Fries adducts were obtained and p-toluenesulfinic and p-toluenesulfonic acids were liberated. The nature and amount of the acid photoreleased were tuned by changing the reaction conditions and the nature and position of the aromatic substituents. In deaerated solutions p-toluenesulfinic acid was formed exclusively, whereas under oxygenated conditions the stronger p-toluenesulfonic acid was released, as shown by HPLC ion chromatography analyses. ArO-S bond photocleavage takes place from the singlet state, as confirmed by laser flash photolysis experiments, and competitive intersystem crossing can make the aryl tosylate unreactive when a nitro group is present. The application of these aryl tosylates as non-ionic photoacid generators (PAGs) in hybrid organic/inorganic sol-gel photoresists has been explored.
Palladium-catalyzed borylation of aryl mesylates and tosylates and their applications in one-pot sequential suzuki-miyaura biaryl synthesis
Chow, Wing Kin,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
supporting information; experimental part, p. 6913 - 6917 (2011/08/03)
Top of the one-pots! The first palladium-catalyzed borylation of aryl tosylates and mesylates is described. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., R=CN, CHO, COOMe, C(O)R, NH2, or NH-indole; see scheme). Pd/MeO-CM-phos allows one-pot sequential reactions in the preparation of unsymmetrical biaryls. Copyright
Suzuki-Miyaura coupling of aryl tosylates and mesylates in water
Pschierer, Jan,Plenio, Herbert
supporting information; experimental part, p. 2934 - 2937 (2010/08/07)
The palladium complex (0.5 mol-%) of a water-soluble sulfonated fluorenylphosphane (cataCXium Fsulf) enables the facile Suzuki-Miyaura coupling of various (heterocyclic) aryl tosylates and aryl mesylate with various (heterocyclic) boronic acids in excellent yields (> 95%) using water as the reaction solvent.
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
