138768-32-8Relevant articles and documents
Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
, p. 3532 - 3538 (2018/08/01)
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
Bi(OTf)3-Catalyzed Multicomponent α-Amidoalkylation Reactions
Schneider, Angelika E.,Manolikakes, Georg
, p. 6193 - 6212 (2015/06/30)
A bismuth(III) triflate catalyzed three-component synthesis of α-substituted amides starting from amides, aldehydes, and (hetero)arenes is reported. The reaction has a broad substrate scope, encompassing formaldehyde as well as aryl and alkyl aldehydes. Low catalyst loadings are required, and water is formed as the only side product. The scope and limitation of this method will be discussed.
A palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents: Synthesis of diarylmethylamines protected by easily removable acyl group
Chen, Qian,Liu, Chao,Guo, Fang,Li, Liang
, p. 5337 - 5340 (2015/07/15)
An efficient process was developed to synthesis diarylmethylamines protected by a readily removable acyl group using a palladium-catalyzed arylation of N-acyl-N,O-acetals with arylboronic reagents. The attractive features of this protocol are: the ease of
Peroxidation of C-H bonds adjacent to an amide nitrogen atom under mild conditions
Yu, Hui,Shen, Jie
supporting information, p. 3204 - 3207 (2014/07/08)
Under mild conditions, the oxidative functionalization of C-H bonds adjacent to an amide nitrogen atom was achieved. tert-Butylperoxyamido acetal was obtained in high yields and could be further converted into α-substituted amides by treatment with Grigna
Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
Yaragorla, Srinivasarao,Singh, Garima,Lal Saini, Pyare,Reddy, M. Kesava
, p. 4657 - 4660 (2014/12/10)
An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.
A Lewis acid palladium(II)-catalyzed three-component synthesis of α-substituted amides
Beisel, Tamara,Manolikakes, Georg
supporting information, p. 6046 - 6049 (2014/01/06)
A Lewis acid palladium-catalyzed reaction of amides, aryl aldehydes, and arylboronic acids is described. This new method allows for a practical and general synthesis of α-substituted amides from simple, readily available building blocks.
Cobalt-catalyzed benzylic C-H amination via dehydrogenative-coupling reaction
Ye, Yang-Hong,Zhang, Ji,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information; experimental part, p. 4649 - 4654 (2011/06/27)
An efficient direct benzylic C-H amination via dehydrogenative-coupling by using an inexpensive catalyst/oxidant (CoBr2/tBuOO tBu) system is described. Various unmodified amides including primary or secondary sulfonamides, carboxamides, and carbamates preformed well with benzylic hydrocarbons with moderate to good yields.
Solvent-free amination of secondary benzylic alcohols with N-nucleophiles catalyzed by FeCl3
Yu, Jian-Jun,Wang, Li-Min,Guo, Feng-Lou,Liu, Jin-Qian,Liu, Ying,Jiao, Ning
experimental part, p. 1609 - 1616 (2011/06/23)
A general, simple, and environmentally friendly method for the direct amination of secondary benzyl alcohols with amides or 4-nitroaniline is described. This method has been applied to a variety of substrates, and the reaction proceeded smoothly at room temperature under solvent-free conditions. CbzNH2 was proved to be very useful in the direct preparation of the benzylic amines from corresponding alcohols.
Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine
Niwa, Takashi,Suehiro, Takafumi,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 5125 - 5131 (2009/11/30)
Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described.
o-Benzenedisulfonimide as a reusable Bronsted acid catalyst for Ritter-type reactions
Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano
experimental part, p. 430 - 436 (2009/07/19)
Reactions between various benzyl alcohols or tert-butyl alcohol and nitriles were carried out in the presence of catalytic amounts (usually 10-20 mol-%) of o-benzenedisulfonimide as a Bronsted acid catalyst; the reaction conditions were mild and the yields of amides were good. The catalyst was easily recovered and purified, ready to be used in further reactions, with economic and ecological advantages. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
