27831-94-3Relevant academic research and scientific papers
Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
Sun, Manman,Chen, Weida,Xia, Xiangyu,Shen, Guodong,Ma, Yongmin,Yang, Jianguo,Ding, Hanfeng,Wang, Zhiming
supporting information, p. 3229 - 3233 (2020/04/10)
A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp2)-H activation, allylic C(sp3)-H activation, and homoallylic C(sp3)-H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.
Vinylogous Elimination/C-H Functionalization/Allylation Cascade Reaction of Allenoate Adducts: Synthesis of Ring-Fused Dihydropyridinones
Sun, Manman,Chen, Weida,Wu, Haijian,Xia, Xiangyu,Yang, Jianguo,Wang, Lei,Shen, Guodong,Wang, Zhiming
supporting information, p. 8313 - 8319 (2020/11/03)
A palladium-catalyzed cascade reaction of β′-allenoate adducts with aryl/heteroaryl carboxamides through a vinylogous elimination/C-H functionalization/intramolecular allylation reaction sequence has been developed with high Z stereoselectivity. Various ring-fused dihydropyridinones bearing an α,β-unsaturated ester substituent are obtained. It is the first example of application of the allenoate adducts to C-H functionalization annulations as practical precursors of hard-to-get functionalized electron-deficient 1,3-butadienes. Using air as the terminal oxidant also shows a great advantage in environmental friendliness.
Synthesis of N-Acyl Sulfamates from Fluorosulfonates and Potassium Trimethylsilyloxyl Imidates
Zhang, Shuning,Xiong, Huan,Lu, Fengping,Ma, Fei,Gu, Yuang,Ma, Peixiang,Xu, Hongtao,Yang, Guang
, p. 15380 - 15388 (2019/11/21)
An efficient and operationally simple method for the synthesis of N-acyl sulfamates from fluorosulfonates and potassium trimethylsilyloxyl imidates as amide precursor is reported. This approach showed broad substrate scope, mild and base-free reaction conditions, short reaction time, and high to excellent yields. Notably, we demonstrated the power of this reaction in the rapid late-stage functionalization of three complex phenol-containing bioactive molecules. Given the prevalence of phenol-containing drugs and building blocks, this method is applicable toward a diversity-oriented drug discovery.
Palladium-Catalyzed C-H Trifluoroethoxylation of N-Sulfonylbenzamides
Yang, Long,Li, Shangda,Cai, Lei,Ding, Yongzheng,Fu, Lei,Cai, Zhihua,Ji, Huafang,Li, Gang
supporting information, p. 2746 - 2749 (2017/05/24)
The trifluoroethyl aryl ethers are important motifs in drug molecules. However, a report devoted specifically to the study of transition-metal-catalyzed C-H trifluoroethoxylation has not been reported to date. A protocol of Pd(II)-catalyzed o-C-H trifluor
Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines
Williamson, Kevin S.,Sawicki, James W.,Yoon, Tehshik P.
, p. 3524 - 3527 (2014/08/18)
We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.
Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions
Ton, Thi My Uyen,Tejo, Ciputra,Tania, Stefani,Chang, Joyce Wei Wei,Chan, Philip Wai Hong
experimental part, p. 4894 - 4904 (2011/08/03)
A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)4Cl2] generated in situ from reaction of FeCl 2 with pyridine.
Development of an acyl sulfonamide anti-proliferative agent, ly573636 ? na
Yates, Matthew H.,Kallman, Neil J.,Ley, Christopher P.,Wei, Jeffrey N.
experimental part, p. 255 - 262 (2010/04/22)
The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlo- robenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.
Direct ionic liquid promoted organocatalyzed diazo-transfer reactions: diversity-oriented synthesis of diazo-compounds
Ramachary, Dhevalapally B.,Narayana, Vidadala V.,Ramakumar, Kinthada
, p. 2704 - 2709 (2008/09/19)
A practical and novel ionic liquid promoted organocatalytic selective diazo-transfer process for the synthesis of highly substituted diazo-compounds in high yields is reported. The ionic liquid can be reused without affecting the reaction rates or yields over five runs.
Solvent effects on the solvolyses of N-benzoyl-arenesulfonimidoyl chlorides
Kutuk, Halil,Tillett, John G.
, p. 35 - 47 (2007/10/03)
Rates of solvolyses of N-benzoyl-arenesulfonimidoyl chlorides have been studied in different compositions of aqueous organic solvents and analysed in terms of the mol fraction of organic solvent, the dielectric constant, the Kirkwood function, the polarisibility, some ENT values, a multiparameter equation and the Grunwald-Winstein equation. All these criteria were consistent with a concerted bimolecular SN2 mechanism of solvolysis.
