61582-64-7Relevant academic research and scientific papers
Spin Trapping as Applied to Radicals Produced by Chemical Reaction. III. Intermediates of the Reactions of Dibenzoyl Peroxide with Diethylamine and Diphenylamine
Nishimura, Norio,Nakamura, Tatsuya,Sueishi, Yoshimi,Yamamoto, Shunzo
, p. 165 - 171 (1994)
The reactions of dibenzoyl peroxide (BPO) with diethylamine (DEA) and diphenylamine (DPA) have been studied by means of an ESR technique combined with spin-trapping.In the case of the DEA/BPO system, diethylnitroxide was formed, while for the DPA/BPO syst
Acid-Promoted Expeditious Syntheses of Aminated Dibenzosultams via Palladium/Norbornene Cooperatively Catalysed C?H Amination/Arylation
Zhao, Shen,Han, Shibo,Du, Guopeng,Zhang, Daopeng,Liu, Hui,Li, Xinjin,Dong, Yunhui,Sun, Feng-Gang
supporting information, p. 2078 - 2083 (2021/03/01)
Herein we reported a protocol to access aminated benzofused sultams through sequential ortho-amination, followed by ipso-arylation of aryl iodide bearing sulfonamide functional group via palladium/norbornene coorperative catalysis. This reaction has showcased a broad spectrum of substrate scope under mild conditions with moderate to good efficiency. (Figure presented.).
Synthesis of C4-Substituted Indoles via a Catellani and C-N Bond Activation Strategy
Zhang, Bo-Sheng,Wang, Fan,Yang, Ying-Hui,Gou, Xue-Ya,Qiu, Yi-Feng,Wang, Xi-Cun,Liang, Yong-Min,Li, Yuke,Quan, Zheng-Jun
supporting information, p. 8267 - 8271 (2020/11/03)
This paper describes the case of a cross study between the C-N bond cleavage reaction field and the Catellani-Lautens reaction system. A series of highly functionalized C4-substituted indoles were synthesized using this strategy. By screening the alkyl groups of amines, the energy barrier of C-N bond cleavage reaction was reduced and the corresponding allenization products were avoided. Finally, the density functional theory calculation shows that the inert C-N bond activation reaction is not a concerted process; on the contrary, the coupling reaction first generates indole quaternary ammonium salt, and then C-N bond cleavage occurs via an SN2 process.
Direct N-O bond formation via oxidation of amines with benzoyl peroxide
Banerjee, Amit,Yamamoto, Hisashi
, p. 2124 - 2129 (2019/02/20)
Herein, we report a general and efficient method for direct N-O bond formation without undesirable C-N bond (amide) formation starting from commercially available amines and benzoyl peroxide. The oxidation of 1,2-diamines to furnish bis-(benzoyloxy)-1,2-diamines is reported for the first time. We found that a significant amount of water (BPO?:?water = 3?:?1) in combination with Cs2CO3 is necessary to achieve high selectivity and yield. The reaction conditions are applicable to a wide range of 1,2-diamine and 1,2-disubstituted-1,2-diamine substrates. Additionally this method is highly applicable to primary and secondary amines. Further, the present method can access chiral bis-hydroxamic acids and bis-hydroxyl amines in just two steps from 1,2-diamines. The reaction conditions are simple, mild and inert atmosphere free. The synthetic potential of this methodology is further demonstrated in the short synthesis of a chiral BHA ligand.
Copper-Catalyzed Dihydroquinolinone Synthesis from Isocyanides and O-Benzoyl Hydroxylamines
Yang, Zhen,Jiang, Kun,Chen, Ying-Chun,Wei, Ye
, p. 3725 - 3734 (2019/03/20)
A copper-catalyzed protocol has been realized for the rapid assembly of dihydroquinolinones from readily accessible isocyanides and O-benzoyl hydroxylamines. The reactions (10 mol % of CuOAc, 10 mol % of dppe, 3 equiv of PhONa, 30 °C) deliver various stru
Copper-Catalyzed Three-Component Carboamination of Arynes: Expeditious Synthesis of o-Alkynyl Anilines and o-Benzoxazolyl Anilines
Niu, Sheng-Li,Hu, Jiangtao,He, Kuicheng,Chen, Ying-Chun,Xiao, Qing
supporting information, p. 4250 - 4254 (2019/06/07)
A copper-catalyzed three-component reaction of in situ formed arynes, terminal alkynes, and O-benzoylhydroxylamines has been developed. By adjusting reaction conditions, the nucleophiles in this transformation can be extended from terminal alkynes to benzoxazoles. These procedures provide a modular and facile approach to o-alkynyl anilines and o-benzoxazolyl anilines from easily available substrates in only one step.
Copper-Catalyzed Electrophilic Ortho C(sp2)-H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System
Begam, Hasina Mamataj,Choudhury, Rajarshee,Behera, Ashok,Jana, Ranjan
supporting information, p. 4651 - 4656 (2019/06/17)
A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, b
Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes
Kato, Kodai,Hirano, Koji,Miura, Masahiro
supporting information, p. 5775 - 5778 (2018/03/27)
A CuCl/(R,R)-PTBP-BDPP-catalyzed regioselective and enantioselective aminoboration of simple and unactivated terminal alkenes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. The amino group and boryl group were incorporated
A Catalyst-Free Amination of Functional Organolithium Reagents by Flow Chemistry
Kim, Heejin,Yonekura, Yuya,Yoshida, Jun-Ichi
supporting information, p. 4063 - 4066 (2018/03/21)
Reported is the electrophilic amination of functional organolithium intermediates with well-designed aminating reagents under mild reaction conditions using flow microreactors. The aminating reagents were optimized to achieve efficient C?N bond formation without using any catalyst. The electrophilic amination reactions of functionalized aryllithiums were successfully conducted under mild reaction conditions, within 1 minute, by using flow microreactors. The aminating reagent was also prepared by the flow method. Based on stopped-flow NMR analysis, the reaction time for the preparation of the aminating reagent was quickly optimized without the necessity of work-up. Integrated one-flow synthesis consisting of the generation of an aryllithium, the preparation of an aminating reagent, and their combined reaction was successfully achieved to give the desired amine within 5 minutes of total reaction time.
O2-Mediated Oxidation of Aminoboranes through 1,2-N Migration
Rauser, Marian,Warzecha, Daniel P.,Niggemann, Meike
supporting information, p. 5903 - 5907 (2018/05/14)
In analogy to the classical reaction of C?B bonds with peroxides, the first oxidative functionalization of aminoboranes through a 1,2-N migration was realized. Readily available aliphatic nitro compounds are thereby transformed into N- and O-functionalized hydroxylamines in a single synthetic operation. Addition of hazardous peroxides is avoided. Instead, the insertion of O2, as the terminal oxidant, into Zn?C bonds provides the necessary peroxides. The required zinc organyls, in turn, are formed through a boron-to-zinc exchange, from an organoboronic ester byproduct of the nitro-to-aminoborane transformation.
