3034-32-0Relevant articles and documents
Zn(II) pyridinyl amine complexes, synthesis and crystal structure studies: A comparative study of the effect of nuclearity and benzoate type on the ring-opening polymerization of cyclic esters
Akintayo, Damilola C.,Jonnalagadda, Sreekantha B.,Munzeiwa, Wisdom A.,Omondi, Bernard
, (2021/12/21)
A series of N-(pyridinylmethyl)aniline Zn(II) carboxylate complexes were synthesized and fully characterized by NMR, IR, mass spectroscopy and elemental analysis. The reaction of the N-(pyridin-4-ylmethyl)aniline ligand (L1) with Zn(II) acetate and benzoi
Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
Airoldi, Veronica,Piccolo, Oreste,Roda, Gabriella,Appiani, Rebecca,Bavo, Francesco,Tassini, Riccardo,Paganelli, Stefano,Arnoldi, Sebastiano,Pallavicini, Marco,Bolchi, Cristiano
supporting information, p. 162 - 168 (2019/12/11)
A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
Solvent-Free N-Alkylation and Dehydrogenative Coupling Catalyzed by a Highly Active Pincer-Nickel Complex
Arora, Vinay,Dutta, Moumita,Das, Kanu,Das, Babulal,Srivastava, Hemant Kumar,Srivastava, Hemant Kumar,Kumar, Akshai,Kumar, Akshai
, p. 2162 - 2176 (2020/06/05)
The synthesis and characterization of a pincer-nickel complex of the type (iPr2NNN)NiCl2(CH3CN) is reported here. We have demonstrated the utility of this pincer-nickel complex (0.02 and 0.002 mol %) for the catalytic N-alkylation of amines using various alcohols. Under solvent-free conditions, while the highest yield (ca. 90%) was obtained for the alkylation of 2-aminopyridine with naphthyl-1-methanol, excellent turnovers (34000 TONs) were observed for the alkylation of 2-aminopyridine with 4-methoxybenzyl alcohol. To demonstrate the synthetic utility of these systems, high-yield reactions (up to 98%) have been probed for representative substrates with a higher loading of the pincer-nickel catalyst (4 mol %). DFT studies indicate that while β-hydride elimination is the RDS for alcohol dehydrogenation, the N-alkylated product can be formed either via hydrogenation with a rate-determining σ-bond metathesis or by alcoholysis that has imine insertion as the RDS. All of the corresponding resting states have been observed by HRMS (ESI) analysis. The labeling experiments are also complementary to DFT studies and show evidence for the involvement of the benzylic C-H bond in the RDS with a kCHH/kCHD value of about 2.5. This method has been applied to accomplish efficient (2000 TONs) dehydrogenative coupling leading to various benzimidazoles.
