90823-94-2Relevant academic research and scientific papers
N-aryl formamide prepared by using ethyl bromodifluoroacetate as formylating reagent
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Paragraph 0037, (2018/12/02)
The invention discloses a compound of N-aryl formamide prepared by using ethyl bromodifluoroacetate as a formylating reagent. The compound is prepared by using N-alkyl arylamine as a raw material, ethyl bromodifluoroacetate as a formylating reagent and copper as a catalyst, adding different ligands, bases, etc., performing reaction under stirring in a reaction solvent at 100-120 DEG C for 10-14 hours; then filtering the reaction solution to obtain filtrate after reaction ending; concentrating the filtrate, removing the solvent by using a rotary evaporator to obtain a residue, treating the residue by silica gel column chromatography, eluting with an eluent, collecting the effluent according to the actual gradient; combining the effluent containing the product, concentrating the combined effluent to remove the solvent, and performing vacuum drying to obtain the target product. The compound has the advantages of simple and easily obtained raw materials, simple preparation process, less pollution, low energy consumption and high yield.
Copper-Catalyzed N-Formylation of Amines through Tandem Amination/Hydrolysis/Decarboxylation Reaction of Ethyl Bromodifluoroacetate
Li, Xiao-Fang,Zhang, Xing-Guo,Chen, Fan,Zhang, Xiao-Hong
, p. 12815 - 12821 (2018/10/20)
Ethyl bromodifluoroacetate (BrCF2COOEt) was first used as the N-formylating reagent in the copper-catalyzed N-formylation of amines. A range of primary, secondary, cyclic arylamines, and aliphatic amines underwent the N-formylation smoothly to furnish the N-formamides in moderate-to-excellent yields.
Visible-light-induced oxidative formylation of N-alkyl-N-(prop-2-yn-1-yl)anilines with molecular oxygen in the absence of an external photosensitizer
Ji, Wangqin,Li, Pinhua,Yang, Shuai,Wang, Lei
supporting information, p. 8482 - 8485 (2017/08/03)
Visible-light-induced oxidative formylation of N-alkyl-N-(prop-2-yn-1-yl)anilines with molecular oxygen in the absence of an external photosensitizer was developed and afforded the corresponding formamides in good yields under mild conditions. The investigation of the mechanism disclosed that both the starting material and the product act as photosensitizers, and 1O2 and O2- are generated through energy transfer and a single electron transfer pathway and play an important role in the reaction.
Cyclisation versus 1,1-carboboration: Reactions of B(c6f 5)3 with propargyl amides
Melen, Rebecca L.,Hansmann, Max M.,Lough, Alan J.,Hashmi, A. Stephen K.,Stephan, Douglas W.
, p. 11928 - 11938 (2013/09/23)
A series of propargyl amides were prepared and their reactions with the Lewis acidic compound B(C6F5)3 were investigated. These reactions were shown to afford novel heterocycles under mild conditions. The reaction of a variety of N-substituted propargyl amides with B(C6F5)3 led to an intramolecular oxo-boration cyclisation reaction, which afforded the 5-alkylidene-4,5-dihydrooxazolium borate species. Secondary propargyl amides gave oxazoles in B(C 6F5)3 mediated (catalytic) cyclisation reactions. In the special case of disubstitution adjacent to the nitrogen atom, 1,1-carboboration is favoured as a result of the increased steric hindrance (1,3-allylic strain) in the 5-alkylidene-4,5-dihydrooxazolium borate species. Copyright
A convenient one-pot synthesis of N-aryl-3-pyrrolines
Jayaprakash, Karamil,Venkatachalam, Chittoor S.,Balasubramanian, Kalpattu K.
, p. 6493 - 6496 (2007/10/03)
N-propargylanilines under one-pot homologation conditions, undergo an in situ cyclisation catalysed by Cu(I) to yield 3-pyrrolines in good yield.
