2446-51-7Relevant academic research and scientific papers
N-Alkoxy Carboxamide Stabilized Tin(II) and Germanium(II) Complexes for Thin-Film Applications
George, Sheby Mary,Nam, Ji Hyeun,Lee, Ga Yeon,Han, Jeong Hwan,Park, Bo Keun,Kim, Chang Gyoun,Jeon, Dong Ju,Chung, Taek-Mo
, p. 5539 - 5546 (2016)
A new series of germanium (1–5) and tin (6–10) complexes were successfully synthesized by employing N-alkoxy-functionalized carboxamides as stabilizing ligands, and these complexes could potentially serve as precursors for thin-film applications. All of t
Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
Tóth, Balázs L.,Sályi, Gerg?,Domján, Attila,Egyed, Orsolya,Bényei, Attila,Gonda, Zsombor,Novák, Zoltán
, p. 348 - 354 (2021/11/09)
The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C-H/N-H annulation of N -methoxy benzamides with saturated ketones
Du, Xiao,Hu, Yuntao,Huang, Decai,Wu, Hailong,Yang, Darun,Yang, Wendi,Zhao, Huaiqing
supporting information, p. 783 - 789 (2022/02/03)
The synthesis of isoindolinones from N-methoxy benzamides and saturated ketones via a bimetallic tandem catalytic annulation has been accomplished. The reaction is catalyzed by a Rh/Cu-cocatalytic system and proceeds via the combination of Cu-catalyzed de
Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones
Wang, Huihong,Cao, Fei,Gao, Weiwei,Wang, Xiaodong,Yang, Yuhang,Shi, Tao,Wang, Zhen
, p. 863 - 868 (2021/02/06)
Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.
Electrodimerization ofN-Alkoxyamides for the Synthesis of Hydrazines
Nasier, Abudulajiang,Chang, Xihao,Guo, Chang
, p. 16068 - 16076 (2021/09/18)
An efficient and valuable N-N dimerization reaction ofN-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, anN-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, variousN-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
Pd/C-catalyzed aerobic oxidative C–H alkenylation of arenes in γ-valerolactone (GVL)
Anastasiou, Ioannis,Ferlin, Francesco,Santoro, Stefano,Vaccaro, Luigi,Viteritti, Orlando
, (2021/08/09)
A novel methodology for the heterogeneous palladium-catalyzed C–H alkenylation of N-methoxybenzamides and anilides is presented. This approach is based on the use of commercially available Pd/C as catalyst and molecular oxygen as terminal oxidant, in comb
Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature
Nielsen, John,Tung, Truong Thanh
supporting information, p. 10073 - 10080 (2021/12/10)
Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is
Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides
Zhang, Xinyu,Lin, Bo,Chen, Jianhui,Chen, Jiajia,Luo, Yanshu,Xia, Yuanzhi
supporting information, p. 819 - 825 (2021/02/01)
The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst
Mayakrishnan, Sivakalai,Tamizmani, Masilamani,Maheswari, Naryanan Uma
supporting information, p. 15462 - 15465 (2020/12/25)
Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.
Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent
Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng
, p. 2645 - 2649 (2019/04/17)
The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.
