- Copper-catalyzed oxidative methylation of sulfonamides by dicumyl peroxide
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A novel and facile copper-catalyzed methylation of sulfonamides was herein demonstrated. The practical transformation took place readily under the oxidative conditions, and N-methyl amides (23 examples) were successfully furnished in high efficiency (up to 90% yields). Dicumyl peroxide was considered to act not only as the oxidant in the system, but also methyl donor for the methylation protocol.
- Che, Shiying,Zhu, Qiao,Luo, Zhenghong,Lian, Yan,Zhao, Zijian
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p. 935 - 942
(2021/01/05)
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- N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]
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A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.
- Liu, Peng,Tung, Nguyen Thanh,Xu, Xiangchao,Yang, Jiazhi,Li, Feng
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p. 2621 - 2631
(2021/02/27)
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- Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate
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An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.
- Liu, Peng,Yang, Jiazhi,Ai, Yao,Hao, Shushu,Chen, Xiaozhong,Li, Feng
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p. 281 - 290
(2021/03/26)
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- Direct Introduction of Sulfonamide Groups into Quinoxalin-2(1H)-ones by Cu-Catalyzed C3-H Functionalization
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Direct sulfonamidation of quinoxalin-2(1H)-one derivatives has been developed using a readily available Cu salt as the catalyst and inexpensive ammonium persulfate as the oxidant in moderate conditions. Owing to the feature of handy operation and good functional group tolerance, this method provides a convenient and efficient access to curative 3-sulfonamidated quinoxalin-2(1H)-one scaffolds.
- Tan, Yushi,Liu, Boyan,Han, Ya-Ping,Zhang, Yuecheng,Zhang, Hong-Yu,Zhao, Jiquan
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supporting information
p. 3365 - 3369
(2020/10/02)
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- Method for synthesizing N-methyl sulfonamide in water
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The invention discloses a method N - for synthesizing,methylsulfamide in water, by using a transition metal iridium catalyst to catalyze N - methylation reaction. by using a non-toxic and harmless water as a solvent, to avoid using the organic agent; to react only as a byproduct, without an environmental hazard; reaction temperature with respect to the previous strip more mild; and have a wide application prospect; with high selectivity, reaction atomic economy.
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Paragraph 0045-0049
(2020/03/12)
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- N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst
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The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.
- Han, Xingyou,Li, Feng,Liu, Peng,Meng, Chong,Tung, Nguyen Thanh
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p. 5815 - 5824
(2020/05/26)
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- Transition-Metal-Free One-Step Synthesis of Ynamides
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A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
- Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
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p. 4458 - 4466
(2019/03/26)
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- Copper(i)-catalyzed N-H olefination of sulfonamides for: N -sulfonyl enaminone synthesis
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This communication reports copper-catalyzed N-H olefination of sulfonamides for enaminone synthesis using saturated ketones as olefin sources. With TEMPO derivatives and O2 as oxidants, this method provided an efficient way to produce various enaminones in good yields. Mechanistic studies helped figure out the stable intermediates and develop novel methodologies for the difunctionalization of saturated ketones.
- Liang, Xiao,Huang, Xin,Xiong, Mingteng,Shen, Kexin,Pan, Yuanjiang
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supporting information
p. 8403 - 8406
(2018/08/03)
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- Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles
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Sulfonated oxindoles are accessed by a Cu(OAc)2-catalyzed three-component reaction of N-(arylsulfonyl)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.
- Wang, Hepan,Sun, Song,Cheng, Jiang
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supporting information
p. 5844 - 5847
(2017/11/10)
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- UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides
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A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.
- Chen, Ming,Yang, Chao,Wang, Yanpei,Li, Dazhi,Xia, Wujiong
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supporting information
p. 2280 - 2283
(2016/06/01)
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- Indolizine Derivatives
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Compounds of formula (I) are ligands of the CRTH2 receptor and are useful in the treatment of respiratory disease: Formula (I) wherein R1, R2, R3 and R4 each independently are hydrogen, C1C6/sub
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Page/Page column 20-21
(2009/07/10)
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- IMDOLIZINE DERIVATIVES AS LIGANDS OF THE CRTH2 RECEPTOR
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Compounds of formula (I) are CRTH2 antagonists, useful in the treatment of, for example, asthma, chronic obstructive pulmonary disease, rhinitis, allergic airway syndrome, and allergic rhinobronchitis. Formula (I) wherein R1, R2. R3 and R4 each independently are hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, halo, -S(O)nR10, -SO2N(R10)2, -N(R10)2, -C(O)N(R10)2, -NR10C(O)R9, -CO2R10, -C(O)R9, -NO2, -CN or -OR11; wherein each R9 is independently C1-C6alkyl, aryl, heteroaryl; R10 is independently hydrogen, C1-C6alkyl, aryl, or heteroaryl; R11 is hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl or a group -SO2R10 ; n is 0, 1 or 2; R5 is C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, optionally substituted aryl, or optionally substituted heteroaryl; R6 is hydrogen, C1-C6alkyl or fully or partially fluorinated C1-C6alkyl ; R7 and R8 are independently hydrogen or C1-C6alkyl, or R7 and R8 together with the atom to which they are attached form a cycloalkyl group; and X is -CHR6-, -S(O)n-, -C(O)-, -NR6SO2- or -SO2NR6- wherein n is 0, 1 or 2.
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Page/Page column 42
(2008/06/13)
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- Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors
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Compounds of the formula which are useful in disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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Page/Page column 26-27
(2010/01/31)
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- Heterocyclic compounds for the treatment of CNS and cardiovascular disorders
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Novel aromatic bicyclic amines of formula (I) STR1 are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.
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