35278-95-6Relevant academic research and scientific papers
Hydrazone complexes of ruthenium(II): Synthesis, crystal structures and catalytic applications in N-alkylation reactions
Murugan, Kaliyappan,Natarajan, Karuppannan,Nirmala, Muthukumaran,Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
, (2020/07/21)
A series of new Ru(II) complexes of 8-hydroxy quinoline-2-carboxyaldehyde hydrazone of the general formula [RuH(CO)(EPh3)2L] (1–6) (E = P or As, L = N’-((8-hydroxyquinolin-2-yl)methylene)thiophene-2-carbohydrazide (HQ-THy), N’-((8-hydroxyquinolin-2-yl)methylene)isonicotinohydrazide (HQ-IHy), N’-((8-hydroxyquinolin-2-yl)methylene) benzohydrazide (HQ-BHy)) have been synthesized. They have been characterized by elemental analysis, IR, NMR (1H, 13C & 31P) and ESI-MS spectral methods. Further, structures of two of the complexes have been determined by single crystal X-ray diffraction technique which revealed a pseudo octahedral geometry with the coordination of the quinoline nitrogen and quinoline oxygen atoms of the ligand. All the new complexes have been employed as efficient catalysts in N-alkylation reactions for the synthesis of tertiary amines by the coupling of secondary amines with aromatic primary alcohols at low catalyst loading with maximum yields. In addition, the effects of substituents on the ligands, different solvents as well as bases and amounts of catalyst loading on the catalytic activity of the complexes have been thoroughly investigated. Complex 1 was found to be efficient catalyst towards N-alkylation of alcohols with the amine. Further, a variety of secondary amines and aromatic (hetero) primary alcohols with various functional groups have also been successfully used in the N-alkylation reactions and it has been found that only one equivalent of the alcohol was consumed in the process.
La[N(sime3)2]3-catalyzed deoxygenative reduction of amides with pinacolborane. scope and mechanism
Barger, Christopher J.,Dicken, Rachel D.,Weidner, Victoria L.,Motta, Alessandro,Lohr, Tracy L.,Marks, Tobin J.
supporting information, p. 8019 - 8028 (2020/05/27)
Tris[N,N-bis(trimethylsilyl)amide]lanthanum (LaNTMS) is an efficient and selective homogeneous catalyst for the deoxygenative reduction of tertiary and secondary amides with pinacolborane (HBpin) at mild temperatures (25-60 °C). The reaction, which yields amines and O(Bpin)2, tolerates nitro, halide, and amino functional groups well, and this amide reduction is completely selective, with the exclusion of both competing inter- and intramolecular alkene/alkyne hydroboration. Kinetic studies indicate that amide reduction obeys an unusual mixed-order rate law which is proposed to originate from saturation of the catalyst complex with HBpin. Kinetic and thermodynamic studies, isotopic labeling, and DFT calculations using energetic span analysis suggest the role of a [(Me3Si)2N]2La-OCHR(NR′2)[HBpin] active catalyst, and hydride transfer is proposed to be ligand-centered. These results add to the growing list of transformations that commercially available LaNTMS is competent to catalyze, further underscoring the value and versatility of lanthanide complexes in homogeneous catalysis.
Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines
Wei, Duo,Netkaew, Chakkrit,Carré, Victor,Darcel, Christophe
, p. 3008 - 3012 (2019/05/15)
An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.
Benzylamines via Iron-Catalyzed Direct Amination of Benzyl Alcohols
Yan, Tao,Feringa, Ben L.,Barta, Katalin
, p. 381 - 388 (2016/01/12)
Benzylamines play a prominent role in numerous pharmaceutically active compounds. Thus, the development of novel, sustainable catalytic methodologies to provide access to these privileged structural motifs is of central importance. Herein we describe a systematic study for the construction of a large variety of benzylamines using a well-defined homogeneous iron complex. The methodology consists of the direct coupling of readily available benzyl alcohols with simpler amines through the borrowing hydrogen methodology, producing a variety of substituted secondary and tertiary benzylamines in moderate to excellent yields for the first time with an iron catalyst. Notably, we explore the versatility of this methodology in the one-pot synthesis of nonsymmetric tertiary amines, sequential functionalization of diols with distinctly different amines, and the synthesis of N-benzyl piperidines via various synthetic pathways. In addition, direct conversion of the renewable building block 2,5-furan-dimethanol to pharmaceutically relevant compounds is achieved.
Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives
Sakai, Norio,Hori, Hiroaki,Yoshida, Yoshihiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 4722 - 4729 (2015/07/27)
We demonstrated a copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals leading to the synthesis of α-aryl glycines and diarylmethylamines. Under an ambient atmosphere, this catalytic system could be applied to the activation of a C(sp3)-O bond of N,O-acetals with an ester and an aryl group, or without a coordinating substituent, as well as to a C(sp3)-N bond of N,N-aminals.
Highly efficient and eco-friendly synthesis of tertiary amines by reductive alkylation of aldehydes with secondary amines over a Pt nanowires catalyst
Wu, Junjie,Lu, Shuanglong,Ge, Danhua,Gu, Hongwei
, p. 81395 - 81398 (2015/10/06)
Plentiful tertiary amine derivates are synthesized by direct formation of tertiary amines by the interaction of aldehydes with secondary amines over Pt nanowires under mild conditions. This method offers a green and rapid approach to transform secondary amines into various tertiary amines.
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.
Ultrasound-assisted solventless synthesis of amines by in situ oxidation/reductive amination of benzyl halides
Khumraksa, Bannarak,Phakhodee, Wong,Pattarawarapan, Mookda
, p. 20454 - 20458 (2014/06/09)
Ultrasound-assisted solventless oxidation/reductive amination of benzyl halides was developed as a facile, efficient, and environmental friendly method toward N-alkylated amines. Aldehydes were formed in situ by oxidation of organic halides with N-methylmorpholine N-oxide (NMO), followed by direct reductive amination with amines using sodium borohydride and montmorillonite K-10 catalyst as the reducing system. This green and simple procedure enables N-alkylated amines to be prepared in good to excellent yields with high selectivity of the monoalkylation. This journal is the Partner Organisations 2014.
Interfacial hydrogenation and deamination of nitriles to selectively synthesize tertiary amines
Lu, Shuanglong,Li, Chao,Wang, Jiaqing,Pan, Yue,Cao, Xueqing,Gu, Hongwei
supporting information, p. 11110 - 11113 (2014/10/15)
A novel one-pot method has been developed for the interfacial hydrogenation of nitriles to synthesize asymmetrical tertiary amines. The active Pt NWs allow for the preparation of a series of tertiary amines in excellent yields (up to 99.0%) and a mixed solvent is vital for the adjustment of the yield. And also, the reaction proceeded under mild conditions and is environmentally friendly.
Zwitterionic-surfactant-stabilized palladium nanoparticles as catalysts in the hydrogen transfer reductive amination of benzaldehydes
Drinkel, Emma E.,Campedelli, Roberta R.,Manfredi, Alex M.,Fiedler, Haidi D.,Nome, Faruk
, p. 2574 - 2579 (2014/04/17)
Palladium nanoparticles (NPs) stabilized by a zwitterionic surfactant are revealed here to be good catalysts for the reductive amination of benzaldehydes using formate salts as hydrogen donors in aqueous isopropanol. In terms of environmental impact and e
