13063-60-0Relevant academic research and scientific papers
Ruthenium Complex Catalyzed N-Heterocyclization. Syntheses of N-Substituted Piperidines, Morpholines, and Piperazines from Amines and 1,5-Diols
Tsuji, Yasushi,Huh, Keun-Tae,Ohsugi, Yukihiro,Watanabe, Yoshihisa
, p. 1365 - 1370 (1985)
1,5-Pentanediol reacts with aliphatic and aromatic primary amines in the presence of a ruthenium catalyst modified with phosphonic ligands to give N-substituted piperidines in fair to goods yields.The reactions were carried out at 150-180 deg C for 5 h in dioxane.The nature of the phosphorus ligands has a remarkable effect on the catalytic activity, For the reaction of aromatic amines, triphenylphosphine is effective, while for aliphatic amine more basic tributyl- or triethylphosphine is preferable.Amines also react with diethylene glycol and N-substituted diethanolamines in the presence of the ruthenium catalyst to give N-substituted morpholines and piperazines in good yields, respectively.
2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines: Selectivity Switching in 8-Quinolinolato Rhodium Catalysis
Morimoto, Yoshihiko,Hamada, Moe,Takano, Shotaro,Mochizuki, Katsufumi,Kochi, Takuya,Kakiuchi, Fumitoshi
, p. 3803 - 3808 (2021/04/05)
Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.
Colloid and Nanosized Catalysts in Organic Synthesis: XVIII.1 Disproportionation and Cross-Coupling of Amines During Catalysis with Immobilized Nickel Nanoparticles
Popov, Yu. V.,Mokhov,Latyshova,Nebykov,Panov,Davydova
, p. 2757 - 2761 (2018/02/21)
It has been stated that immobilized nickel nanoparticles catalyze disproportionation and cross-coupling of amines. The influence of the support on the catalysis of these properties in the in plug-flow reactor has been studied. The use of active carbon as the support has been found advantageous for the cross-coupling of amines, whereas alumina was a better support for the disproportionation reaction.
P-cymenesulphonyl chloride: A bio-based activating group and protecting group for greener organic synthesis
Farmer, Thomas J.,Clark, James H.,Gothe, Maite L.,Macquarrie, Duncan J.,Sherwood, James
, p. 1914 - 1919 (2015/09/22)
A bio-derived protecting/activating group has been synthesized by introducing a sulphonyl chloride group to the aromatic ring of p-cymene derived from citrus peel waste. The resulting p-cymenesulphonyl chloride was evaluated as an activating group by reacting with 1-octanol, 2-octanol, phenol and piperidine, and further reactions of the activated alcohols. The comparison to tosyl chloride demonstrates that the bio-based alternative can be effectively utilized as a direct replacement for the current fossil derived equivalent.
Base-promoted N-alkylation using formamides as the N-sources in neat water
Chen, Wen-Xin,Zhang, Cai-Yun,Shao, Li-Xiong
, p. 880 - 885 (2014/01/23)
An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.
Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia
Cui, Xinjiang,Dai, Xingchao,Deng, Youquan,Shi, Feng
supporting information, p. 3665 - 3675 (2013/03/29)
The N-alkylation of amines or ammonia with alcohols is a valuable route for the synthesis of N-alkyl amines. However, as a potentially clean and economic choice for N-alkyl amine synthesis, non-noble metal catalysts with high activity and good selectivity are rarely reported. Normally, they are severely limited due to low activity and poor generality. Herein, a simple NiCuFeOx catalyst was designed and prepared for the N-alkylation of ammonia or amines with alcohol or primary amines. N-alkyl amines with various structures were successfully synthesized in moderate to excellent yields in the absence of organic ligands and bases. Typically, primary amines could be efficiently transformed into secondary amines and N-heterocyclic compounds, and secondary amines could be N-alkylated to synthesize tertiary amines. Note that primary and secondary amines could be produced through a one-pot reaction of ammonia and alcohols. In addition to excellent catalytic performance, the catalyst itself possesses outstanding superiority, that is, it is air and moisture stable. Moreover, the magnetic property of this catalyst makes it easily separable from the reaction mixture and it could be recovered and reused for several runs without obvious deactivation. Copyright
Anti-Markovnikov addition of both primary and secondary amines to terminal alkynes catalyzed by the TpRh(C2H4)2/PPH 3 system
Fukumoto, Yoshiya,Asai, Harumi,Shimizu, Masaki,Chatani, Naoto
, p. 13792 - 13793 (2008/04/04)
Terminal alkynes react with secondary amines in the presence of TpRh(C2H4)2/PPh3 (Tp = trispyrazolylborate) to give anti-Markovnikov E-enamines. Both Tp and PPh3 ligands are essential for the reaction. The reaction tolerates functional groups, such as ester, nitrile, and siloxy groups, on the terminal alkynes. Primary amines also add to terminal alkynes in anti-Markovnikov fashion, yielding the corresponding imines. The formation of a vinylidene-rhodium complex followed by the intermolecular nucleophilic attack by an amine nitrogen at the α-carbon atom of the vinylidene-metal intermediate may be involved in a key step in the catalytic reaction. Copyright
Nickel-catalyzed electrophilic amination of organozinc halides
Berman, Ashley M.,Johnson, Jeffrey S.
, p. 1799 - 1801 (2007/10/03)
The nickel-catalyzed electrophilic amination of organozinc halides with O-benzoyl N,N-dialkyl hydroxylamines allows for the preparation of a variety of aryl and alkyl tertiary amines in good yield. The reaction is noteworthy for the mild reaction conditions employed (room temperature) and the ease of product purification (acid/base extractive work up). Georg Thieme Verlag Stuttgart.
N-alkyl ammonium acetonitrile bleach activators
-
, (2008/06/13)
Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.
Nematocidal activity of long alkyl chain amides, amines and their derivatives on dog roundworm larvae
Kiuchi,Nishizawa,Kawanishi,Kinoshita,Ohsima,Uchitani,Sekino,Ishida,Kondo,Tsuda
, p. 3234 - 3244 (2007/10/02)
The nematocidal activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached a maximum at an optimal chain length and decreased in both shorter and longer homologues. The relationship between the activity and hydrophobicity of the homologues was analysed by the use of the bilinear model. The hydrophobicity of a compound, which gives a maximal activity, was similar for all neutral amides, but amides which have an additional amine group in the molecule had different values. Tertiary amines and their salts having a long alkyl chain also showed nematocidal activities comparable to those of the corresponding amides. The salts killed the larva at concentrations lower than their critical micell concentration, suggesting that they behave as a single molecule for the nematocidal action.
