Relevant bibliographies by topics / Catalytic hydroamination

Academic literature on the topic 'Catalytic hydroamination'

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Published: 4 June 2021
Last updated: 21 February 2023

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Journal articles on the topic "Catalytic hydroamination"

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Palchak, Zachary L., Daniel J. Lussier, Conor J. Pierce, Hoseong Yoo, and Catharine H. Larsen. "Catalytic Tandem Markovnikov Hydroamination-Alkynylation and Markovnikov Hydroamination-Hydrovinylation." Advanced Synthesis & Catalysis 357, no. 2-3 (January 30, 2015): 539–48. http://dx.doi.org/10.1002/adsc.201401037.

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Pohlki, Frauke, and Sven Doye. "The catalytic hydroamination of alkynes." Chemical Society Reviews 32, no. 2 (January 22, 2003): 104–14. http://dx.doi.org/10.1039/b200386b.

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Severin, René, and Sven Doye. "The catalytic hydroamination of alkynes." Chemical Society Reviews 36, no. 9 (2007): 1407. http://dx.doi.org/10.1039/b600981f.

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Brunet, Jean-Jacques, Ngoc Châu Chu, Ousmane Diallo, and Emmanuelle Mothes. "Catalytic intermolecular hydroamination of alkenes." Journal of Molecular Catalysis A: Chemical 198, no. 1-2 (May 2003): 107–10. http://dx.doi.org/10.1016/s1381-1169(02)00734-3.

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Isaeva, Vera I., and Leonid M. Kustov. "Catalytic Hydroamination of Unsaturated Hydrocarbons." Topics in Catalysis 59, no. 13-14 (August 2016): 1196–206. http://dx.doi.org/10.1007/s11244-016-0640-9.

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Smolensky, Elena, Moshe Kapon, and Moris S. Eisen. "Catalytic Intermolecular Hydroamination of Methylenecyclopropanes." Organometallics 24, no. 23 (November 2005): 5495–98. http://dx.doi.org/10.1021/om050518h.

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Roesky, Peter W., and Thomas E. Müller. "Enantioselective Catalytic Hydroamination of Alkenes." Angewandte Chemie International Edition 42, no. 24 (June 23, 2003): 2708–10. http://dx.doi.org/10.1002/anie.200301637.

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Tussing, Sebastian, Miriam Ohland, Garrit Wicker, Ulrich Flörke, and Jan Paradies. "Borane-catalyzed indole synthesis through intramolecular hydroamination." Dalton Transactions 46, no. 5 (2017): 1539–45. http://dx.doi.org/10.1039/c6dt04725d.

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Gallegos, Carlos, Ruth Camacho, Mercedes Valiente, Tomás Cuenca, and Jesús Cano. "Cyclopentadienyl-based Mg complexes in the intramolecular hydroamination of aminoalkenes: mechanistic evidence for cationic versus neutral magnesium derivatives." Catalysis Science & Technology 6, no. 13 (2016): 5134–43. http://dx.doi.org/10.1039/c5cy01040c.

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Palchak, Zachary L., Daniel J. Lussier, Conor J. Pierce, Hoseong Yoo, and Catharine H. Larsen. "ChemInform Abstract: Catalytic Tandem Markovnikov Hydroamination-Alkynylation and Markovnikov Hydroamination-Hydrovinylation." ChemInform 46, no. 26 (June 2015): no. http://dx.doi.org/10.1002/chin.201526044.

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Dissertations / Theses on the topic "Catalytic hydroamination"

1

Shasha, Adelle. "Metal-Catalysed Hydroamination." Science. School of Chemistry, 2007. http://hdl.handle.net/2123/1710.

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Doctor of Philosophy(PhD),
This thesis describes the synthesis of terminal and internal amino and amidoalkynes and their hydroamination (cyclisation) catalysed by the complex (bis(N-methylimidazol-2-yl)methane)dicarbonylrhodium(I) tetraphenylborate (1). A series of analogous palladium complexes were also prepared and investigated for catalytic hydroamination. The scope of the rhodium(I) complex (1) for the intramolecular hydroamination of more complex amino and amidoalkyne substrates was investigated. This was made possible with the synthesis of aliphatic substrates, namely, 4 pentyn 1 amide (3) and 5 hexyn 1 amide (4) and a number of aromatic substrates, namely, 1, 4 diamino-2, 5 diethynylbenzene (5), 1, 4-diamino-2, 5 bis(phenylethynyl)benzene (6), 2, 3-diamino-1, 4-diethynylbenzene (7), 2, 3-diamino-1, 4-bis(phenylethynyl)benzene (8), 1, 5-bis(acetamido)-2, 4-diethynylbenzene (9), N-(acetyl)-2-ethynylbenzylamine (10) and N-(acetyl)-2-(phenylethynyl)benzylamine (11). The rhodium(I) complex (1) catalytically cyclised the aliphatic 4 pentyn 1 amide (3) regioselectively to the 6 membered ring, 3, 4 dihydro 2 pyridone (64) as the sole product. Attempts to cyclise 5 hexyn 1 amide (4) to produce either the 6 or 7 membered ring were unsuccessful. Compounds 5, 6, 7 and 8 were doubly cyclised to 1, 5 dihydro pyrrolo[2, 3 f]indole (71), 1, 5-dihydro-2, 6-diphenyl-pyrrolo[2, 3 f]indole (73), 1, 8-dihydro-pyrrolo[2, 3 g]indole (74) and 1, 8-dihydro-2, 7-diphenyl-pyrrolo[2, 3 g]indole (75) respectively. The aromatic amides with terminal acetylenes 9 and 10 cyclised to give 1, 7 diacetyl pyrrolo[3, 2 f]indole (76) and N (acetyl) 1, 2 dihydroisoquinoline (77) respectively. However, attempts to cyclise 11 were unsuccessful. Thus the rhodium(I) complex (1) successfully catalysed via hydroamination both terminal and internal acetylenic amine and amide substrates, to give pyridones, indoles and isoquinolines. Cationic and neutral palladium complexes incorporating the bidentate heterocyclic nitrogen donor ligand bis(N-methylimidazol-2-yl)methane (bim; 2) were synthesised: [Pd(bim)Cl2] (15), [Pd(bim)2][BF4]2 (17) [Pd(bim)(Cl)(CH3)] (14), [Pd(bim)(CH3)(NCCH3)][BF4] (16). All of the complexes were active as catalysts for the intramolecular hydroamination reaction, using the cyclisation of 4 pentyn 1 amine (21) to 2 methyl 1 pyrroline (22) as the model test reaction. Percentage conversions, turnover numbers and reaction profiles for each complex were compared to the rhodium(I) complex (1). These studies have shown that the catalytic activity was not significantly dependent on the bim donor ligand or the choice of metal. Substitution of the bim (2) ligand with the COD ligand and the use of methanol as the solvent did impact significantly on the efficiency of the hydroamination reactions.
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Shasha, Adelle. "Metal-Catalysed Hydroamination." Thesis, The University of Sydney, 2006. http://hdl.handle.net/2123/1710.

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This thesis describes the synthesis of terminal and internal amino and amidoalkynes and their hydroamination (cyclisation) catalysed by the complex (bis(N-methylimidazol-2-yl)methane)dicarbonylrhodium(I) tetraphenylborate (1). A series of analogous palladium complexes were also prepared and investigated for catalytic hydroamination. The scope of the rhodium(I) complex (1) for the intramolecular hydroamination of more complex amino and amidoalkyne substrates was investigated. This was made possible with the synthesis of aliphatic substrates, namely, 4 pentyn 1 amide (3) and 5 hexyn 1 amide (4) and a number of aromatic substrates, namely, 1, 4 diamino-2, 5 diethynylbenzene (5), 1, 4-diamino-2, 5 bis(phenylethynyl)benzene (6), 2, 3-diamino-1, 4-diethynylbenzene (7), 2, 3-diamino-1, 4-bis(phenylethynyl)benzene (8), 1, 5-bis(acetamido)-2, 4-diethynylbenzene (9), N-(acetyl)-2-ethynylbenzylamine (10) and N-(acetyl)-2-(phenylethynyl)benzylamine (11). The rhodium(I) complex (1) catalytically cyclised the aliphatic 4 pentyn 1 amide (3) regioselectively to the 6 membered ring, 3, 4 dihydro 2 pyridone (64) as the sole product. Attempts to cyclise 5 hexyn 1 amide (4) to produce either the 6 or 7 membered ring were unsuccessful. Compounds 5, 6, 7 and 8 were doubly cyclised to 1, 5 dihydro pyrrolo[2, 3 f]indole (71), 1, 5-dihydro-2, 6-diphenyl-pyrrolo[2, 3 f]indole (73), 1, 8-dihydro-pyrrolo[2, 3 g]indole (74) and 1, 8-dihydro-2, 7-diphenyl-pyrrolo[2, 3 g]indole (75) respectively. The aromatic amides with terminal acetylenes 9 and 10 cyclised to give 1, 7 diacetyl pyrrolo[3, 2 f]indole (76) and N (acetyl) 1, 2 dihydroisoquinoline (77) respectively. However, attempts to cyclise 11 were unsuccessful. Thus the rhodium(I) complex (1) successfully catalysed via hydroamination both terminal and internal acetylenic amine and amide substrates, to give pyridones, indoles and isoquinolines. Cationic and neutral palladium complexes incorporating the bidentate heterocyclic nitrogen donor ligand bis(N-methylimidazol-2-yl)methane (bim; 2) were synthesised: [Pd(bim)Cl2] (15), [Pd(bim)2][BF4]2 (17) [Pd(bim)(Cl)(CH3)] (14), [Pd(bim)(CH3)(NCCH3)][BF4] (16). All of the complexes were active as catalysts for the intramolecular hydroamination reaction, using the cyclisation of 4 pentyn 1 amine (21) to 2 methyl 1 pyrroline (22) as the model test reaction. Percentage conversions, turnover numbers and reaction profiles for each complex were compared to the rhodium(I) complex (1). These studies have shown that the catalytic activity was not significantly dependent on the bim donor ligand or the choice of metal. Substitution of the bim (2) ligand with the COD ligand and the use of methanol as the solvent did impact significantly on the efficiency of the hydroamination reactions.
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Courtney, Sarah Turner. "Trifluoromethylated zirconium amidate complexes : new directions for the catalytic hydroamination of alkenes." Thesis, University of British Columbia, 2009. http://hdl.handle.net/2429/9704.

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Hydroamination is the addition of an N–H bond across a C–C multiple bond. Nitrogen containing small molecules, typically accessed through multi-step synthetic pathways, are greatly important to both the pharmaceutical and fine chemical industries. Hydroamination is a rapidly expanding field due to the recent emphasis on sustainable chemistry for industrial applications as it provides an atom economical route to N-heterocycles, imines and amines. Group 4 catalysts have been greatly successful in this area however, intramolecular hydroamination of aminoalkenes typically proceeds only under high temperature reaction conditions. Low temperature reactivity is preferred from a practical perspective and is targeted here as a valuable probe to identify precatalysts most likely to display intermolecular alkene reactivity. The facile synthesis of organic amides provides a desirable means to adjust and optimize the steric and electronic properties of the proligand framework. Trifluoromethyl groups have been identified as desirable electron-withdrawing ligand substituents for the generation of reactive electrophilic zirconium hydroamination precatalysts. Proligand synthetic investigations revealed unforeseen challenges due to the electronic and steric effects imparted by trifluoromethyl substituents and unfortunately, the attractive 2,4,6-tris(trifluoromethyl) aryl-amides are of limited practical usefulness. In complex synthesis, the structure, bonding and reactivity screening of these novel electrophilic zirconium complexes will be presented as well as challenges associated with increased solubility. Importantly, these fluorinated systems have been shown to enhance reactivity of zirconium bis(amidate)bis(amido) complexes in the intramolecular hydroamination of alkenes. Progress toward low temperature (65 °C) reactivity will be discussed.
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Lau, Ying Yin. "Catalytic synthesis of N-heterocycles and alpha-alkylated amines by hydroamination and hydroaminoalkylation." Thesis, University of British Columbia, 2016. http://hdl.handle.net/2429/60156.

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The research presented in this thesis emphasizes the versatility and utility of N,O-chelated early transition metals for the catalytic synthesis of -alkylated amines. Two major transformations were studied extensively in this work, hydroamination and hydroaminoalkylation. For both reactions, the synthetic utility and substrate scope has been expanded by the work presented herein. In the field of hydroamination, N-heterocycles with more than one heteroatom can now be synthesized using early transition metal catalysts from prochiral substrates. Hydroamination with a bis(amidate)bis(amido) complex of titanium of ether-containing aminoalkyne substrates yield cyclic imines, which are subsequently reduced via asymmetric transfer hydrogenation using the Noyori-Ikariya catalyst, RuCl [(S,S)-Ts-DPEN] (η⁶-p-cymene). 3-Substituted morpholines are synthesized using a one-pot sequential catalysis protocol, in good yields and high enantiomeric excesses. Substrate scope investigations reveal that high enantioselectivities in the asymmetric transfer hydrogenation reaction arise from key hydrogen bonding interactions between the oxygen heteroatom of the ether-containing cyclic imine and the [(S,S)-Ts-DPEN] ligand of Noyori-Ikariya catalyst. This mechanistic insight informed the proposal that this synthetic strategy can be extended to other substrates containing functional groups with hydrogen bond acceptors. As such, 3-substituted piperazines are also prepared with high enantioselectivities using this one-pot protocol. Advances to the hydroaminoalkylation transformation have also been made with the first reported example of room temperature reactivity observed using a phosphoramidate-tantalum complex. The preparation and characterization of a series of N,O-chelated phosphoramidate-tantalum complexes is described. These complexes were easily synthesized from either Ta(NMe₂)₅ by protonolysis or a simple organometallic precursor, TaMe₃Cl₂, by salt metathesis. Reactivity towards catalytic hydroaminoalkylation was explored and the results highlight that the choice of tantalum starting material dramatically affects the reaction temperatures required for catalytic turnover. N,O-chelated phosphoramidate dimethylamido tantalum complexes showed reactivity occurred only at elevated temperatures (≥ 90 °C), whereas phosphoramidate-tantalum complexes derived from TaMe₃Cl₂ exhibited unprecedented catalytic activity at room temperature. Preliminary efforts indicate that there is potential for an asymmetric version of hydroaminoalkylation at room temperature. Chiral phosphoramidate-tantalum complexes were prepared and studied as the first examples of asymmetric hydroaminoalkylation reactions at room temperature.
Science, Faculty of
Chemistry, Department of
Graduate
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Moran, Erik John. "Novel Synthetic Routes to Complex Amines: the Catalytic Hydroamination of Alkynes and Hydroimination of Allenes." Thesis, North Dakota State University, 2016. https://hdl.handle.net/10365/28036.

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Amines are valuable targets for synthesis in contexts of both research and industrial applications. This work proposes two atom-economical methods—hydroamination (HAM) and hydroimination (HIM)—as C-N bond formation strategies. A nickel-(N-heterocyclic carbene) catalyst system was developed to carry out HAM of internal, unactivated alkynes with aryl amines and cyclic secondary amines. It was demonstrated that the Ni-NHC catalyst was capable of promoting both HAM at room temperature and transfer hydrogenation to produce α-branched aryl amines. These two procedures were performed by the same catalyst to demonstrate an elegant 1-pot, multi-transformation protocol. Separately, optimization of a Rh-HIM catalyst system for the combination of monosubstituted allenes and aromatic N-H-ketimine was carried out to favor high conversion of substrates to the linear HIM product rather than [3+2] annulation. Both HAM and HIM C-N bond formation methods were found to be successful and capable of good conversion and selectivity for their respective products.
NSF (CHE-1301409 to R.M.) and ND-EPSCoR (RII-1330840)
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Wixey, James S. "Novel calcium complexes applied to intramolecular hydroamination catalysis." Thesis, Cardiff University, 2012. http://orca.cf.ac.uk/37858/.

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This thesis discusses the synthesis, characterisation, and reactivity studies of a range of new chiral calcium complexes supported by various polydentate N-donor ligands and their suitability as catalysts for intramolecular hydroamination. Chapter One outlines the case for developing organocalcium complexes, including a general overview of their current application to a variety of heterofunctionalisation reactions. Chapter Two introduces the chiral ethylene diamines which are extensively used as calcium supporting ligands and later as precursors for the synthesis of bisimidazoline and potential imoxazoline ligands. Chapter Two provides details of the diamine synthesis and includes studies related to racemisation concerns of the chiral centre. Chapter Three discusses novel calcium complexes supported by the chiral ethylene diamine analogues presented in Chapter Two. Complex synthesis, characterisation, and catalytic performance in intramolecular hydroamination is probed and discussed. Chapter Four details a range of new bisimidazoline ligands and their employment as supporting ligands on calcium. The catalytic performance of the resulting complexes in intramolecular hydroamination is subsequently analysed and discussed. Chapter Five investigates the attempted development of a total synthetic pathway to a new class of imoxazoline ligand and related issues. Chapter Six contains all experimental procedures, characterising data pertaining to all new compounds and complexes presented in this Thesis. Appendices A-K contain additional catalytic figures and tables of crystallographic data for all new crystallographically characterised compounds. Summary sheets of every literature and new compound presented mentioned in this Thesis are also included, along with copies of both printed publications resulting from this Thesis at the time of submission.
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Thomson, Robert Kenneth. "Amidate complexes of the group 4 metals : sythesis, reactivity, and hydroamination catalysis." Thesis, University of British Columbia, 2008. http://hdl.handle.net/2429/1344.

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A series of bidentate amidate ligands with variable groups R' and R" abbreviated by [R"(NO)R'] and adamantyl substituted tetradentate amidate ligands abbreviated by Ad[0₂N₂] were utilized as ancillaries for Ti, Zr, and Hf. Protonolysis routes into homoleptic amidate complexes, tris(amidate) mono(amido), bis(amidate) bis(amido), and bis(amidate) dibenzyl complexes are high yielding when performed with tetrakis(amido) and tetrabenzyl group 4 starting materials. Many of these complexes have been characterized in both the solid-state and in the solution phase, where in the latter case these complexes are fluxional and undergo exchange processes. Multiple geometric isomers are possible with the mixed N,0 chelate provided by the amidate ligands, and geometric isomerization of bis(amidate) bis(amido) complexes has been examined through X-ray crystallographic and density functional theory (DFT) calculations. Isomerization is dictated largely by the steric bulk present at the N of the amidate ligands, and is proposed to proceed through a K²-K¹-K² ligand isomerization mechanism, which is supported by crystallographic evidence of K¹-bound amidate ligands. The amidate ligand system binds to these metals in a largely electrostatic fashion, with poor orbital overlap, generating highly electrophilic metal centers. The bis(amidate) dibenzyl complexes of Zr and Hf are reactive towards insertion, abstraction, and protonolysis. Insertion of isocyanides into the Zr-C bonds of [DMP(NO) tBu]₂Zr(CH₂Ph₂ results in the formation of ƞ₂-iminoacyl complexes, which can either undergo thermally induced C=C coupling to generate an enediamido complex (aryl isocyanides), or rearrange to generate a bis(amidate) bis(vinylamido) complex (alkyl isocyanides). Benzyl abstraction to generate cationic Zr bis(amidate) benzyl complexes is also possible through reaction with [Ph₃C][B(C₆F₅)4] or B(C₆F₅)₃ Terminal imido complexes with novel pyramidal geometries are generated through protonolysis of bis(amidate) bis(amido) Ti and Zr complexes with primary aryl amines. DFT calculations demonstrate the existence of a Zr⁻₌N triple bond for these complexes. Dimeric imido complexes have been characterized in the solid state, but are not maintained in solution. Cycloaddition reactions of the terminal Zr imido complexes with C=0 bonds result in the formation of proposed oxo complexes and organic metathesis products. Catalytic aminoalkene cyclohydroamination has also been realized with these complexes, generating N-heterocyclic products. A series of kinetic and labeling studies support an imido-cycloaddition mechanism for catalytic cyclohydroamination of primary aminoalkenes with neutral bis(amidate) Ti and Zr precatalysts. The intermediate Ti imido complex, K²-[Dipp(NO)tBu-K¹_[DiPP(No) tBu]Ti=NCH₂CPh₂CH₂CH=CH₂(NHMe₂), has been isolated and characterized in the solid-state and in solution. Amine stabilized imido complexes of this type are invoked as the resting state for the catalytic reaction, and solution phase data support a chair-like geometry, where the alkene is coordinated to the metal center. A diastereoselectivity study supports this proposed solution structure. Eyring and Arrhenius parameters, as well as isolation of a 7-coordinate model imido complex, support a seven-coordinate transition state for the rate-determining metallacycle protonolysis reaction. In contrast, secondary aminoalkene hydroamination catalysis with cationic Zr benzyl complexes is proposed to proceed through a σ-bond insertion mechanism. Proton loss from cationic Zr amido complexes to generate imido species is proposed with primary aminoalkenes, and the resultant neutral imido complexes can catalyze the cyclization of these substrates by the aforementioned imido-cycloaddition mechanism. The ability of the amidate ligand system to promote both mechanisms is unique in the field of alkene hydroamination catalysis.
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Brown, Adam Ross. "I. Engaging Cationic Intermediates in Asymmetric Catalysis: Enantioselective Reactions of Carbenium Ions and N,N-Dialkyliminium Ions II. Enantioselective Catalysis of the Cope-Type Hydroamination by H-Bond Donors." Thesis, Harvard University, 2013. http://dissertations.umi.com/gsas.harvard:11009.

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The research described here explores the ability of dual H-bond donor catalysts to induce asymmetry in a variety of synthetically useful transformations that proceed via diverse reactive intermediates. In Chapters 1-3, we investigate ureas and thioureas as anion-binding catalysts for asymmetric reactions that proceeed via cationic intermediates with little precedent as electrophiles in asymmetric catalysis. Chapter 4 details our application of H-bond donor catalysis to the Cope-type hydroamination. Chapter 1 describes the development of an asymmetric aldehyde alkylation catalyzed by a bifunctional primary aminothiourea. A variety of 2-aryl propionaldehydes are alkylated with benzhydryl bromides in moderate to good yields and good enantioselectivities. Catalyst structure-activity relationship studies of the alkylation pointed towards electrophile activation by the dual H-bond donor moiety. Experiments aimed at gaining a better understanding of the electophile activation mode and characterizing the activated electrophilic intermediate in the alkylation reaction are described in Chapter 2. The development of an enantioselective cyanide addition to N,N-dialkyliminium intermediates is the subject of Chapter 3. A variety of strategies for accessing N,N- dialkyliminium ions are established, and chiral thioureas are shown to promote the addition of cyanide to such intermediates with moderate enantioselectivities. Chapter 4 details our discovery that thioureas bearing polarizable and conformationally constrained aromatic groups catalyze highly enantioselective Cope-type hydroaminations. This powerful transformation provides a variety of chiral pyrrolidine products under mild reaction conditions.
Chemistry and Chemical Biology
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Loiseau, Francis. "Cope-type Hydroamination of Alkenes with Hydroxylamines and Hydrazines - Scope and Mechanism." Thèse, Université d'Ottawa / University of Ottawa, 2013. http://hdl.handle.net/10393/23794.

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Hydroamination stands as a desirable approach to nitrogen-containing molecules, which have important applications ranging from pharmaceuticals (fine chemicals) to paints, coatings, insecticides and agrochemicals (bulk chemicals). It features the use of alkene and alkyne starting materials, which are abundant and rarely used in the formation of C-N bonds. This work aims at building on the improved Cope-type reactivity developed in the Beauchemin group by expanding the reach of the reaction and understanding its mechanistic complexities. The first part of this thesis describes the development of cascade reactions to provide a thermodynamic driving force for the intermolecular Cope-type hydroamination of alkenes. The methodology serves as a proof of concept that the dipolar reaction intermediates can be engineered to further react irreversibly to more stable products, and has shown potential in improving the syntheses of natural alkaloids. The second part of the thesis describes the expansion of Cope-type hydrazide hydroaminations through a systematic investigation of hydrazine analogs as reactants. Optimized reagents are featured in the first reported intermolecular Cope-type hydrohydrazidation of alkenes. Mechanistic investigations and isolation of ammonium ylide intermediates support a 5-membered concerted and planar mechanistic pathway for hydrazide hydroaminations, similar to that observed with hydroxylamines. The final section presents mechanistic data disproving a previously assumed difficult proton transfer step in the hydroamination using hydroxylamines. From such findings, early results are presented towards a hydrogen-bond catalyzed hydroamination, which has potential applicability across the field of Cope-type hydroaminations and beyond.
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Bilodeau, Didier Alexandre. "Exploiting Intramolecularity: Exploring Aldehyde-Catalyzed Intermolecular Hydroaminations and Mixed Aminal Chemistry." Thesis, Université d'Ottawa / University of Ottawa, 2018. http://hdl.handle.net/10393/37100.

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Hydroamination reactions are very attractive to form new C-N bonds, though broadly applicable synthetic methods do not exist. The hydroamination of unactivated alkenes is especially difficult to accomplish given its negative reaction entropy, as well as potentially being a thermodynamically unfavourable transformation with some substrates. Thus, previously reported systems have often consisted of biased intramolecular systems or metal-catalyzed intermolecular variations operating at low temperatures. Recently, our group discovered that intermolecular Cope-type hydroamination of unactivated alkenes is achievable through the use of aldehydes as catalysts. These organocatalysts act solely through promoting the pre-association of reacting partners, hydroxylamines and allyl amines, in order to induce temporary intramolecularity; thus allowing for very mild reaction conditions and access to important 1,2-Diamine motifs. This thesis presents studies expanding upon initial reports of aldehyde-catalyzed Cope-type intermolecular hydroamination. In the scope of these studies standard conditions were developed to compare aldehyde catalytic activity. These evaluations led to further strengthening our understanding of hypothesized trends in aldehydes’ catalytic efficiencies, notably the impact of electronic, steric and solvent effects. Furthermore, the possibility of using a catalytic precursor species for hydroamination was evaluated. While this symmetrical hydroxylamine dimer precursor did not result in increased hydroamination yields, it did allow for easier manipulations as well as allow preliminary kinetic isotope effect studies to study formaldehyde as a precatalyst. These KIE studies allowed to reconfirm that hydroamination was highly likely the rate determining step of our proposed catalytic cycle. Derivatization of hydroamination products was also accomplished to access important 1,2 Diamine motifs from simple starting materials, also allowing to access difficult hydroamination products through the application of quantitative amounts of aldehyde, followed by hydrolysis of the formed heterocycles. Additional studies into nitrone reactivity led us to access a novel synthesis of enantiomerically enriched chiral cyclic nitrones through a sequence of nucleophilic addition, Cope-type hydroamination and Cope elimination. However, this sequence proved unpractical and of very narrow applicability, while affording only modest enantioselectivities (up to 78% ee), therefore further exploration was not warranted. A collaborative study was also undertaken in collaboration with the Wennemers group from ETH Zurich. This exploratory study had the goal of examining the potential for combining small peptide catalysis with aldehyde catalysis inducing temporary intramolecularity. It was hypothesized that the combination of both catalytic systems could improve upon the conjugate addition of nucleophiles to certain electrophiles, such as nitroolefins; in a potentially stereoselective manner. Although initial trials did not yield productive reactions, evidence for potential new mixed aminals with formaldehyde and various nucleophiles was found. Furthermore, the background reactivity of various nucleophile and electrophile pairings was assessed, allowing for better calibration of future efforts in studying such systems.
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Books on the topic "Catalytic hydroamination"

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Antonio, Togni, and Grützmacher Hansjörg, eds. Catalytic heterofunctionalization: From hydroanimation [i.e. hydroamination] to hydrozirconation. Weinheim: Wiley-VCH, 2001.

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Togni, Antonio, and Hansjörg Grützmacher. Catalytic Heterofunctionalization: From Hydroamination to Hydrozirconization. Wiley & Sons, Incorporated, John, 2020.

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Togni, Antonio, and Hansjörg Grützmacher. Catalytic Heterofunctionalization: From Hydroamination to Hydrozirconization. Wiley & Sons, Incorporated, John, 2001.

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Book chapters on the topic "Catalytic hydroamination"

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Li, Tianshu, Jelena Wiecko, and Peter W. Roesky. "Zinc-Catalyzed Hydroamination Reactions." In Zinc Catalysis, 83–118. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2015. http://dx.doi.org/10.1002/9783527675944.ch5.

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Färber, T., Arno Behr, and Andreas J. Vorholt. "Hydroamination and Telomerisation of β-Myrcene." In Catalysis by Metal Complexes, 177–89. Cham: Springer International Publishing, 2017. http://dx.doi.org/10.1007/978-3-319-54161-7_10.

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Chen, Zhiwei, and Vy M. Dong. "Rhodium(I)-Catalyzed Hydroformylation and Hydroamination." In Rhodium Catalysis in Organic Synthesis, 49–62. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2019. http://dx.doi.org/10.1002/9783527811908.ch3.

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Beweries, T., and U. Rosenthal. "Catalytic Hydroamination of Alkynes." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...), 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-102-00056.

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"1.4.5 Hydroamination." In N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1, edited by Nolan and Cazin. Stuttgart: Georg Thieme Verlag, 2018. http://dx.doi.org/10.1055/sos-sd-223-00179.

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Shi, Feng, and Xinjiang Cui. "N -Alkyl Amine Synthesis by Hydroamination of Alkene and Diene." In Catalytic Amination for N-Alkyl Amine Synthesis, 75–116. Elsevier, 2018. http://dx.doi.org/10.1016/b978-0-12-812284-6.00003-2.

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Armstrong, Douglas, Bala Ramanathan, Yanhui Shi, and Aaron L. Odom. "Pyrrole Derivatives via Catalytic Hydroamination of 1,4- and 1,5-Diynes." In 19th International Congress on Heterocyclic Chemistry, 112. Elsevier, 2003. http://dx.doi.org/10.1016/b978-0-08-044304-1.50104-0.

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Hussein Mekni, Nejib Ben, and Noureddine Raouafi. "Coordination, Degrading Agent, Catalyst Property and Spectroscopy of Organocalcium Compounds." In The Synthetic Methods, Structures, and Properties of the Ca-Cσ Bond Organocalcium Containing Compounds, 56–82. BENTHAM SCIENCE PUBLISHERS, 2022. http://dx.doi.org/10.2174/9789815040647122010006.

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In addition to the coordination of the calcium to the n electron pairs, some examples of coordination to the π electron pairs are observed resulting from calcium interactions with highly conjugated systems. The complex structures vary from ordinary to close to the unexpected organocalcium inverse sandwich. The organocalcium Ca-C bond containing compounds are highly reactive. They degrade and act as degrading agents on the solvent. The study of the effect of five factors: temperature, concentration, organic group, counter ion and coordinated donor solvent, shows an intramolecular degradation mechanism. Organocalcium complexes are more stable in the THP than in the THF ethereal media. Calcium and organocalcium Ca-Cσ-bond containing derivatives are described as efficient pre-catalysts for catalytic conversions of alkenes by polymerization, hydroamination, hydrosilylation, hydrogenation, and hydrophosphination. The activation process is suggested as an electrostatic interaction between the alkene and Lewis acidic calcium metallic species, leading to both vertical and horizontal polarization of the π bond electron density, resulting in an incentive for nucleophilic attack. Some researchers illustrate that the organocalcium derivatives may be described as “Trojan horses” X-ray constitutes the most efficient technique to characterize the organocalcium structures for crystalized compounds, affording interesting information about angle values and bond lengths. The 43Ca, 13C and 1H NMR spectroscopy constitutes an alternative, secondary and complementary tool for characterizing both soluble, and even insoluble compounds, monitoring the reaction progress and making specific experimental manipulations. The coupling constants 1 JCa-C, and 2 JCa-C-H are not mentioned and there is no mass spectrometry nor IR spectroscopy studies
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Taber, Douglass F. "Arrays of Stereogenic Centers: The Shin/Chandrasekhar Synthesis of (+)-Lactacystin." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0042.

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Kami L. Hull of the University of Illinois established (J. Am. Chem. Soc. 2014, 136, 11256) conditions for the diastereoselective hydroamination of 1 with 2 to give 3. Jon C. Antilla of the University of South Florida employed (Org. Lett. 2014, 16, 5548) an enantiomerically-pure Li phosphate to direct the opening of the prochiral epoxide 4 to 5. Jordi Bujons and Pere Clapés of IQAC-CSIC engineered (Chem. Eur. J. 2014, 20, 12572) an enzyme that mediated the enantioselective addition of glycolaldehyde 7 to an aldehyde 6, leading to 8. Takahiro Nishimura of Kyoto University set (J. Am. Chem. Soc. 2014, 136, 9284) the two stereogenic centers of 11 by adding 10 to the diene 9. Amir H. Hoveyda of Boston College added (J. Am. Chem. Soc. 2014, 136, 11304) the propargylic anion derived from 13 to the aldehyde 12 to give, after oxida­tion, the diol 14. Yujiro Hayashi of Tohoku University constructed (Adv. Synth. Catal. 2014, 356, 3106) 17 by the combination of 15 with 16. Yitzhak Apeloig and Ilan Marek of Technion-Israel Institute of Technology prepared (J. Org. Chem. 2014, 79, 12122) the bromo diol 20 by rearranging the adduct between the alkyne 19 and the acyl silane 18. James P. Morken, also of Boston College, effected (J. Am. Chem. Soc. 2014, 136, 17918) enantioselective coupling of 22 with the bis-borane 21. The prod­uct allyl borane added to benzaldehyde to give the alcohol 23. Sentaro Okamoto of Kanagawa University reduced (Org. Lett. 2014, 16, 6278) the aryl oxetane 24 to an intermediate that coupled with allyl bromide to give the alco­hol 25. In the presence of catalytic CuCN, the alternative diastereomer was the major product. Erick M. Carreira of ETH Zürich used (Angew. Chem. Int. Ed. 2014, 53, 13898) a combination of an Ir catalyst and an organocatalyst to couple the aldehyde 27 with the allylic alcohol 26. The four possible combinations of enantiomerically pure catalysts worked equally well, enabling the preparation of each of the four enan­tiomerically pure diastereomers of 28.
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Jiménez, O., T. E. Müller, W. Schwieger, and J. A. Lercher. "Hydroamination reactions catalysed with beta zeolites." In Studies in Surface Science and Catalysis, 2788–94. Elsevier, 2004. http://dx.doi.org/10.1016/s0167-2991(04)80555-x.

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