84108-98-5Relevant academic research and scientific papers
Efficient visible-light photocatalytic aerobic oxidation of cyclic sulfamides to imines
Ming, Zong-Yao,Li, Kang-Rui,Meng, Fan-Jie,Shi, Lei,Jiang, Wen-Feng
supporting information, (2020/06/17)
A highly efficient photocatalytic aerobic oxidation of cyclic sulfamides to synthesize cyclic N-sulfonyl imines with Ir(ppy)2(dtbpy)PF6 as photocatalyst is reported. These environmentally friendly transformations exihibit good to excellent isolated yields and good generality with respect to both five-membered and six-membered cyclic sulfamides.
Sultam compound and preparation method thereof
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Paragraph 0054-0057; 0105-0107, (2019/11/12)
The invention provides a sultam compound and a preparation method thereof. The method provided by the invention specifically comprises the following steps: putting a catalyst C, sulfamide B and an oxidant D into an organic solvent, performing a reaction,
Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation
Zhong, Dayou,Wu, Di,Zhang, Yan,Lu, Zhiwu,Usman, Muhammad,Liu, Wei,Lu, Xiuqiang,Liu, Wen-Bo
supporting information, p. 5808 - 5812 (2019/08/26)
Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)-H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams.
Reductions of Imines Using Zirconocene Chloride Hydride
Vargová, Denisa,Mudráková, Brigita,Némethová, Ivana,?ebesta, Radovan
, p. 7606 - 7612 (2019/12/03)
Herein, we describe the fast, chemoselective, and clean reduction of imines with zirconocene chloride hydride. The reaction works well on aromatic and enolizable aliphatic aldimines, as well as ketimines. A range of N-protecting groups and various functio
B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines
Shi, Lei,Bao, Robert Li-Yuan,Zheng, Limin,Zhao, Rong
, p. 6550 - 6556 (2019/10/22)
A metal-free method for reduction of cyclic N-sulfonyl ketimines catalyzed by B(C6F5)3, using commercially available methylphenylsilane as a reducing reagent under mild conditions has been developed. This reductive protoco
Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source
Gao, Yang,Zhang, Xuexin,Laishram, Ronibala Devi,Chen, Jingchao,Li, Kangkui,Zhang, Keyang,Zeng, Guangzhi,Fan, Baomin
supporting information, p. 3991 - 3997 (2019/08/02)
A Co-catalyzed effective transfer hydrogenation of various α-ketoesters and N-cyclicsulfonylimides by safe and environmentally benign H2O as hydrogen source is described. The reaction used easily available and easy to handle zinc metal as a reductant. Interestingly, the catalytic system does not require ligand for reduction of N-cyclicsulfonylimides. (Figure presented.).
Nitrene transfer catalyzed by a non-heme iron enzyme and enhanced by non-native small-molecule ligands
Goldberg, Nathaniel W.,Knight, Anders M.,Zhang, Ruijie K.,Arnold, Frances H.
supporting information, p. 19585 - 19588 (2019/12/24)
Transition-metal catalysis is a powerful tool for the construction of chemical bonds. Here we show that Pseudomonas savastanoi ethylene-forming enzyme, a non-heme iron enzyme, can catalyze olefin aziridination and nitrene C-H insertion, and that these activities can be improved by directed evolution. The non-heme iron center allows for facile modification of the primary coordination sphere by addition of metal-coordinating molecules, enabling control over enzyme activity and selectivity using small molecules.
Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex
Seo, Chris S. G.,Tannoux, Thibault,Smith, Samantha A. M.,Lough, Alan J.,Morris, Robert H.
, p. 12040 - 12049 (2019/10/02)
Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.
Vancomycin-iridium (III) interaction: An unexplored route for enantioselective imine reduction
Facchetti, Giorgio,Pellegrino, Sara,Bucci, Raffaella,Nava, Donatella,Gandolfi, Raffaella,Christodoulou, Michael S.,Rimoldi, Isabella
, (2019/08/07)
The chiral structure of antibiotic vancomycin (Van) was exploited as an innovative coordination sphere for the preparation of an IrCp* based hybrid catalysts. We found that Van is able to coordinate iridium (Ir(III)) and the complexation was demonstrated by several analytical techniques such as MALDI-TOF, UV, Circular dichroism (CD), Raman IR, and NMR. The hybrid system so obtained was employed in the Asymmetric Transfer Hydrogenation (ATH) of cyclic imines allowing to obtain a valuable 61% e.e. (R) in the asymmetric reduction of quinaldine 2. The catalytic system exhibited a saturation kinetics with a calculated efficiency of Kcat/KM = 0.688 h?1mM?1
Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis
Tao, Ye,Gilbertson, Scott R.
supporting information, p. 11292 - 11295 (2018/10/26)
The bis(trifluoromethane)sulfonimide (Tf2NH) catalyzed intramolecular hydroamidation of terminal alkynes is reported. The combination of Et3SiH and Tf2NH provides cis-1,3-disubstituted isoindolines and sultams in high yield (up to 98%) and high diastereoselectivity (up to 99?:?1 d.r.).
