19340-96-6Relevant articles and documents
Formation of imines by selective gold-catalysed aerobic oxidative coupling of alcohols and amines under ambient conditions
Kegnaes, Soren,Mielby, Jerrik,Mentzel, Uffe V.,Christensen, Claus H.,Riisager, Anders
, p. 1437 - 1441 (2010)
The formation of imines by aerobic oxidative coupling of mixtures of alcohols and amines was studied using gold nanoparticles supported on titanium dioxide, TiO2, as a heterogeneous catalyst. The reactions were performed at ambient conditions (room temperature and atmospheric pressure) and occurred with excellent selectivity (above 98%) at moderate conversion under optimized conditions. The effect of catalytic amounts of different bases was studied, along with reaction temperature and time. Utilisation of a selective catalyst system that uses dioxygen as an oxidant and only produces water as by-product represents a new green reaction protocol for imine formation.
Ionic liquid effects on a multistep process. Increased product formation due to enhancement of all steps
Keaveney, Sinead T.,Haines, Ronald S.,Harper, Jason B.
, p. 8925 - 8936 (2015)
The reaction of a series of substituted benzaldehydes with hexylamine was examined in acetonitrile and an ionic liquid. In acetonitrile, as the electron withdrawing nature of the substituent increases, the overall addition-elimination process becomes fast
Expanding Coefficient: A Parameter to Assess the Stability of Induced-Fit Complexes
Talotta, Carmen,Concilio, Gerardo,De Rosa, Margherita,Soriente, Annunziata,Gaeta, Carmine,Rescifina, Antonio,Ballester, Pablo,Neri, Placido
supporting information, p. 1804 - 1808 (2021/03/08)
Here we propose a new parameter, the Expanding Coefficient (EC), that can be correlated with the thermodynamic stability of supramolecular complexes governed by weak secondary interactions and obeying the induced-fit model. The EC values show a good linear relationship with the log Kapp of the respective pseudorotaxane complexes investigated. According to Cram's Principle of Preorganization, the EC can be considered an approximate mechanical measure of the host's reorganization energy cost upon adopting the final bound geometry.
One-Pot Construction of Diverse β-Lactam Scaffolds via the Green Oxidation of Amines and Its Application to the Diastereoselective Synthesis of β-Amino Acids
Yamamoto, Yuki,Kodama, Shintaro,Nishimura, Riku,Nomoto, Akihiro,Ueshima, Michio,Ogawa, Akiya
, p. 11571 - 11582 (2021/08/20)
In this study, a simple one-pot construction of β-lactam scaffolds was successfully achieved via 4,6-dihydroxysalicylic acid-catalyzed organocatalytic oxidation of amines to imines using molecular oxygen. Although some imines are highly unstable and difficult to isolate by conventional methods, the organocatalytic oxidation of amines described herein, followed by their direct reaction with acyl chlorides in the presence of a base, afforded a series of new β-lactam derivatives with excellent cis selectivity, which could not be synthesized and isolated by previously reported methods. Thus, this one-pot protocol will be one of the powerful methods applicable to the synthesis of various potential drug candidates and functional molecules. Furthermore, the subsequent hydrolysis of these β-lactams successfully afforded the corresponding β-amino acids as almost single diastereomers in up to 99% yields.
Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
Paudel, Keshav,Xu, Shi,Hietsoi, Oleksandr,Pandey, Bedraj,Onuh, Chuka,Ding, Keying
supporting information, p. 418 - 426 (2021/02/01)
Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.
