Reductive amination reactionKnown as reductiveAmineAlcoholsAldehydesSynthesisCatalystsArenesReactionAbstractAminesHalidesAromaticHydrogenOrganicBiochemistryCatalyticNitrogenDirectMethodIndustryMetalReductive aminationPalladium-Catalyzed AminationBuchwald-Hartwig AAmmoniaEnantioselectiveCatalystDeprotonationPathwayStudiesIron
Reductive amination reaction1
- In the critically acclaimed drama Breaking Bad, main character Walter White uses the reductive amination reaction to produce his high purity methamphetamine, relying on phenyl-2-propanone and methylamine. (wikipedia.org)
Known as reductive2
- Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. (wikipedia.org)
- They draw inspiration from a common synthetic method known as reductive amination (Figure 1). (chembites.org)
Amine3
- Johnson Matthey offers amination catalysts for oxo-alcohol production and for speciality amine production under its HTC™ and PRICAT™ brands. (matthey.com)
- Both reactive manifolds can meet at this point, and the aldehyde (1) can be converted to the alkylated amine product (7) directly via an enzyme-catalyzed reductive amination using a reductive aminase and the biological reductant NADPH as a source of electrons. (chembites.org)
- While we have shown before that the ammonium ions rapidly react with methanol to produce methylammonium ions, these results show that also methoxy groups formed from methanol at strong Brønsted acid sites under reaction conditions are very low, it is concluded that the contribution of the methoxy group amination to the amine formation is very small. (utwente.nl)
Alcohols3
- A protocol for the dehydrative amination of alcohols in water using a water-soluble calix[4]resorcinarene sulfonic acid as a reusable multifunctional catalyst allows an environmentally benign synthesis of benzylic and allylic amines. (organic-chemistry.org)
- Potential elementary reaction steps in solid acid catalyzed amination of light alcohols are critically compared using hydrogen mordenite as (model) catalyst and the open mechanistic questions have been addressed. (utwente.nl)
- Veefkind, VA & Lercher, JA 1999, ' on the elementary steps of acid zeolite catalyzed amination of light alcohols ', Applied catalysis A: general , vol. 181, no. 2, pp. 245-255. (utwente.nl)
Aldehydes1
- Additively manufactured catalytic static mixers were used for the intensified reductive amination of aldehydes and ketones inside a continuous flow reactor. (vapourtec.com)
Synthesis5
- A classic named reaction is the Mignonac reaction (1921) involving reaction of a ketone with ammonia over a nickel catalyst for example in a synthesis of 1-phenylethylamine starting from acetophenone: Nowadays, one-pot reductive amination fulfil by acid-metal catalysts that act as a hydride transfer. (wikipedia.org)
- Reductive amination is predominantly used for the synthesis of the amino acid glutamate starting from α-ketoglutarate, while biochemistry largely relies on transamination to introduce nitrogen in the other amino acids. (wikipedia.org)
- The metal-catalyzed amination of aryl and alkenyl electrophiles has developed into a widely used methodology for the synthesis of natural products, active pharmaceutical ingredients, agricultural chemicals, and materials for molecular electronics. (stanford.edu)
- Chiral amines are broadly used compounds in pharmaceutical industry and organic synthesis, and reductive amination reactions have been the most appreciated methods for their syntheses. (sustech.edu.cn)
- Synthesis of N-Substituted 3-Amino-4-halopyridines: A Sequential Boc-Removal/Reductive Amination Mediated by Brønsted and Lewis Acids. (acs.org)
Catalysts2
- Our amination catalysts are used for a variety of speciality amines production and downstream of our oxo-alcohol catalysts. (matthey.com)
- In this work, based on the Xiao's racemic transfer hydrogenative reductive amination in 2010 and our recent work in novel chiral pyridine ligands, chiral half-sandwich iridium catalysts were rationally designed and synthesized. (sustech.edu.cn)
Arenes4
- C-H amination is the most powerful method to directly add nitrogen functionalities into a variety of arenes including biology- and materials-oriented molecules. (rsc.org)
- Recent developments in aromatic C-H amination chemistry have enabled the conversion of unactivated arenes into a range of arylamine derivatives without using directing groups or excess amounts of arenes. (rsc.org)
- A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). (ntu.edu.sg)
- A mechanistic investigation into the amination of electron-neutral and electron-rich arenes using organic photoredox catalysis is presented. (unc.edu)
Reaction3
- This approach, known as direct reductive amination (Borch reaction), employs reducing agents that only react slowly (or not at all) with the ketone/aldehyde precursors. (wikipedia.org)
- When applied to a broad series of triflate and triflimide salts, the last descriptor allowed a qualitative description of catalytic activity trends for the model amination reaction of benzyl alcohol with aniline. (cardiff.ac.uk)
- Adding alkyl groups to amines constitutes an essential step en route to many pharmaceuticals, agrochemicals, resins, and polymers, but current methods require large amounts of compounds, high temperatures, long reaction times, or the use of toxic or expensive reagents. (chembites.org)
Abstract1
- abstract = "The amination of a diamond surface was investigated by treatment of chlorinated diamond in an ammonia environment at various temperatures. (elsevierpure.com)
Amines1
- Pd-Catalyzed intramolecular allylic C-H amination of 1,1-disubstituted alkenyl amines with various allylic tethers (X = O, NMs, CH 2 ) was developed. (figshare.com)
Halides2
- Optimal experimental conditions for the amination of aryl and alkenyl halides with all classes of nitrogen nucleophiles are presented. (stanford.edu)
- X. Huang and Buchwald, S. L. " New Ammonia Equivalents for the Pd-Catalyzed Amination of Aryl Halides " , Org. (mit.edu)
Aromatic1
- In this perspective, we discuss recent developments in the radical C-H amination of aromatic molecules. (rsc.org)
Hydrogen1
- Halogen bonding induces an intermolecular Csp 3 -H amination and even enables a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. (organic-chemistry.org)
Organic2
- Copper-Catalyzed Amination of Aryl and Alkenyl Electrophiles is intended to provide organic chemists with an accessible, but detailed, introduction to this important class of transformations. (stanford.edu)
- Nonetheless, it is remarkable to witness the synergy between biological systems and organic chemical platforms like reductive amination. (chembites.org)
Biochemistry1
- In biochemistry, dehydrogenase enzymes can catalyze the reductive amination of α-keto acids and ammonia to yield α-amino acids. (wikipedia.org)
Catalytic1
- Particularly noteworthy is the use of substrates containing a labile allylic moiety and new simple catalytic systems capable of promoting highly chemo- and regioselective allylic C-H amination by overcoming significant challenges. (figshare.com)
Nitrogen1
- At an amination temperature of 573 K, most of the nitrogen on the surface was present as imines. (elsevierpure.com)
Direct1
- However, one-step transfer hydrogenative direct asymmetric reductive amination (THDARA) that could expand the scope, simplify the operation and eliminate the use of additives has been challenging. (sustech.edu.cn)
Method1
- This method is sometimes called indirect reductive amination. (wikipedia.org)
Industry1
- Sponge iron was produced from steel mill and amination industry wastes, and valuable mineral products were extracted from sources as flue dusts and uranium tailings. (cdc.gov)
Metal1
- A metal-free sequential dual oxidative amination of C(sp 3 )-H bonds under ambient conditions affords imidazo[1,5-a]pyridines in very good yields. (organic-chemistry.org)
Reductive amination10
- Amination can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductive amination and the Mannich reaction. (wikipedia.org)
- Cobalt-rhodium heterobimetallic nanoparticles catalyze a tandem reductive amination of aldehydes with nitroaromatics without any additives under mild conditions (1 atm H 2 and 25 C). This procedure can be scaled up to the gram scale, and the catalyst can be reused more than six times without loss of activity. (organic-chemistry.org)
- A rapid construction of enantioenriched benzo-fused quinolizidines, indolizidines, and their analogues by ruthenium-catalyzed asymmetric cascade hydrogenation/reductive amination of quinolinyl- and quinoxalinyl-containing ketones has been developed. (unboundmedicine.com)
- TY - JOUR T1 - Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. (unboundmedicine.com)
- In this case, an alternative to reductive amination. (galchimia.com)
- Most organic chemists have probably carried out at least one reductive amination during their career. (galchimia.com)
- The usual sequence for the introduction of a dialkylaminomethyl group on an (hetero)aromatic ring involves the use of an aldehyde, which in turn can be prepared from a bromide derivative by metallation and trapping with DMF, with an amine under reductive amination conditions. (galchimia.com)
- Awarded for the development of new biocatalysts for asymmetric reductive amination, from fundamental understanding of mechanism and structure to applications on an industrial scale. (rsc.org)
- Dichotomy of Atom-Economical Hydrogen-Free Reductive Amidation vs Exhaustive Reductive Amination. (acs.org)
- The work described here developed a high-yield synthesis of chemically stable interstrand cross-links resulting from a reductive amination reaction between an abasic site and the noncanonical nucleobase 2-aminopurine in duplex DNA. (nih.gov)
Palladium-Catalyzed Amination1
- M. H. Ali and Buchwald, S. L. " An Improved Method for the Palladium-Catalyzed Amination of Aryl Iodides " , J. Org. (mit.edu)
Buchwald-Hartwig A3
- A new protocol for palladium-catalyzed Buchwald-Hartwig amination of aryl chlorides and bromides with benzophenone imine as ammonia surrogate is described. (huji.ac.il)
- A previously unaddressed transformation of M/NHC complexes under typical conditions of the Buchwald-Hartwig amination is disclosed. (ananikovlab.ru)
- The Buchwald-Hartwig amination ( BHA ) reaction is an important to form arylnitrogen bonds, specially, to produce aniline which is employed as precursor for pharmaceutical compounds. (usp.br)
Ammonia4
- Yangjian Quan, Zuowei Xie, The Chinese University of Hong Kong, China, and colleagues have developed a reaction for the selective B-H amination of ortho -carboranes using ammonia. (chemistryviews.org)
- The present invention relates to a process for preparing alkanolamines by homogeneously catalyzed alcohol amination of diols by means of ammonia with elimination of water in the presence of a complex catalyst which comprises at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one phosphorus donor ligand. (justia.com)
- The economically attractive amination of diols by means of ammonia to form alkanolamines has not been described for these systems. (justia.com)
- It is an object of the present invention to provide a process for preparing alkanolamines by alcohol amination of diols by means of ammonia with elimination of water. (justia.com)
Enantioselective1
- Here we report the directed evolution of an iron-containing enzymatic catalyst-based on a cytochrome P450 monooxygenase-for the highly enantioselective intermolecular amination of benzylic C-H bonds. (sdsc.edu)
Catalyst3
- Experimental and theoretical studies of the C-H amination reaction mediated by the iron dipyrrinato complex (AdL)FeCl(OEt2) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. (researcher-app.com)
- Grossman, O, Rueck-Braun, K & Gelman, D 2008, ' Trans-spanned palladium catalyst for mild and efficient amination of aryl halides with benzophenone imine ', Synthesis , no. 4, pp. 537-542. (huji.ac.il)
- Depending on the structures of the NHC and azanide, the N-NHC coupling can make a significant contribution to the M/NHC catalyst decomposition in the Buchwald-Hartwig and other amination reactions conducted in the presence of strong bases. (ananikovlab.ru)
Deprotonation1
- The catalytic cycle has four steps: amination step ( tsN ), deprotonation step ( tsH ), reductive elimination step ( RE ) and the final step is oxidative addition step ( OA ). (usp.br)
Pathway1
- According to the researchers, the work provides a new pathway for the direct, efficient, and regioselective B-H amination of ortho -carboranes. (chemistryviews.org)
Studies1
- In these studies, the amination is carried out at 100-180° C. (justia.com)
Iron1
- Sponge iron was produced from steel mill and amination industry wastes, and valuable mineral products were extracted from sources as flue dusts and uranium tailings. (cdc.gov)