Poisoning effect of N-containing compounds on performance of Raney nickel in transfer hydrogenation
The effect of amines, imines and heterocycle compounds on conversion has been studied in transfer hydrogenation of camphor and 2-PrOH catalyzed by Raney nickel. Small amount (5 mol% to nickel) of N-containing compound significantly decreases catalyst activity. It has been shown that the poisoning effect mostly depends on molecular size of amines and heterocyclic compounds. For aniline and cyclohexylamine the dependence of camphor conversion on poison/nickel ratio was obtained. Additionally, benzaldehyde, cinnamaldehyde demonstrated higher reactivity compared corresponding imines under transfer hydrogenation conditions. Obtained data explain low activity of nickel-based catalysts when N-containing compounds are presented in reaction mixture.
Martyanov, Oleg N.,Philippov, Alexey A.
(2021/10/19)
Electrochemical oxidative annulation of amines and aldehydes or ketones to synthesize polysubstituted pyrroles
A general and practical protocol to synthesize polysubstituted pyrroles has been established by electrooxidative annulation of amines and aldehydes or ketones. In an undivided cell, arylacetaldehydes and primary amines can participate in this transformati
Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines
A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.
Zultanski, Susan L.,Zhao, Jingyi,Stahl, Shannon S.
supporting information
p. 6416 - 6419
(2016/06/09)
First efficient two-step/one-pot zirconium (IV)isopropoxide-mediated reductive amination of carbonyl compounds
An efficient method for the synthesis of various primary and secondary amines through a zirconium(IV) isopropoxide-mediated reductive amination reaction of aldehydes and ketones is reported. A series of different aldehydes, ketones and amines were used leading to the expected amino products in moderate to excellent yields. The mechanistic rationale of this reaction has been postulated through the formation of a transient imine species and a diastereoselective version using (R)-phenylethylamine as chiral inducer led to the expected products in moderate to excellent yields and with diastereoselectivities up to 100%.
Pieri, Cyril,Brunel, Jean Michel
p. 448 - 456
(2015/06/22)
The addition of amines to diisobutylaluminum-imine complexes. Preparation of NPS R-568 hydrochloride
A facile procedure for the preparation of secondary and tertiary amines from nitriles has been developed. The addition of amines to diisobutylaluminum-imine complexes derived by treating nitriles with DIBAL-H was found to proceed in moderate to good yield
Barmore, Robert M.,Logan, Sarah R.,Van Wagenen, Bradford C.
p. 3451 - 3454
(2007/10/03)
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