Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Taylor, Jason G.; Adrio, Luis A.; Hii, King Kuok

doi:10.1039/b918970j

Cited by 100 publications

(46 citation statements)

References 41 publications

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“…The result demonstrates the absence of any acidinduced transformation. There are reports warning of the possible action of acids as hydroamination catalysts [18,19] but they all concern less challenging processes such as intramolecular hydroaminations or the intermolecular addition across activated C=C bonds. Furthermore, the conditions employed here are not really acidic, as the amount of acid is a fraction of that of the amine (150 vs. 350 equiv.…”

Section: (C) Catalysis Of Transalkylation Processesmentioning

confidence: 99%

Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination

2011

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PtBr2/nBu4PBr (without solvent) or K2PtCl4/NaBr (in water) have been shown to efficiently catalyze the hydroamination of ethylene by aniline and are poor catalysts for the hydroamination of ethylene by diethylamine. A DFT study on the hydroamination mechanism indicates that the energetic span of the C2H4/Et2NH catalytic cycle is close to that of the C2H4/PhNH2 cycle. The poor performance is attributed to rapid catalyst degradation with reduction to metallic platinum. Pt0, on the other hand, catalyzes a transalkylation process, partially transforming Et2NH into Et3N, EtNH2 and NH3. This process is inhibited by C2H4. Mechanistic considerations for the Pt0‐catalyzed transalkylation process are presented.

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Section: (C) Catalysis Of Transalkylation Processesmentioning

confidence: 99%

Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination

2011

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“…It was found that M 23 (B,C) 6 precipitates reduce the notch impact toughness in C–Mn–Mo steels when the boron content is 10–50 wt ppm. Boron may increase the susceptibility to temper embrittlement (TE) of steels in the tempering temperature range of 400–600 °C, more so in the absence of Mo . In oil‐quenched quench and tempered (QT) steels containing ≈0.003 wt% solute boron, boron was found to adversely affect the impact properties in larger cross sections, i.e., 26–51 mm bar diameter.…”

Section: Effect Of Boron On Toughness and Possible Mechanismsmentioning

confidence: 99%

Boron in Heat‐Treatable Steels: A Review

Sharma

Ortlepp

Bleck

2019

steel research int.

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The science and technology of boron addition to heat‐treatable steels are explained. The aim is to address the following: How to add boron to steel (i.e., the manufacturing aspects of boron addition to steel)? What precautions are necessary when alloying boron to steel, in terms of composition (mainly nitrogen, aluminum, and titanium contents), processing and heat treatment (i.e., material and process robustness and reproducibility for a consistent steel quality)? Where does boron go in steel (i.e., the state of boron, interstitial or substitutional solute, precipitate or a complex with other alloying elements; as well as the location of boron, i.e., dissolved as a solute in the grain or segregated at the grain boundary)? Which characterization methods are suitable for the detection of the very small amounts of boron (<30 wt ppm) in heat‐treatable steels? What does boron do in steel (i.e., its effect on hardenability and mechanical properties, specifically impact toughness)? How does it do and what it does (i.e., the physical mechanism by which it influences the properties)? How much boron is really required to achieve the desired properties in heat‐treatable steels (i.e., recommendations for the optimum boron content)?

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“…[6] Compared to the catalytic processes related to intramolecular hydroaminations, the corresponding intermolecular reactions have been less studied since controlling the regioselectivity (Markovnikov vs. anti-Markovnikov selectivity) is challenging. [7] On the other hand, Gunnoe and coworkers described the anti-Markovnikov addition of aniline to styrene derivatives by using a well-defined copperamido catalyst [8] complexed with an N-heterocyclic carbene (NHC) ligand. The regioselectivity of Cu-catalyzed hydroaminations is known to be influenced by the catalytic system.…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed Intermolecular Hydroamination of Arylamines or Aza‐Heterocycles with Nitrostyrene Derivatives

2019

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A new copper-catalyzed protocol for the intermolecular anti-Markovnikov addition of arylamines or heterocycles to terminal and unsymmetrical 1,2-disubstituted vinylarenes has been developed. The direct hydroamination is catalyzed by a readily available N-heterocyclic carbene-based copper complex and KOt-Bu, and the use of MeOH as an additive enhances the reactivity. The method provides a broad range of new and versatile amine compounds bearing various functional groups in good to excellent yields. a] Reaction conditions: nitrostyrene 1 a (0.40 mmol), amine 2 (0.48 mmol), MeOH (0.40 mmol), IPrCuCl (5 mol%), KOt-Bu (5 mol%), toluene (1.0 M) under N 2 . [b] Yields of the isolated products. The reaction time was 7 h for 3 aa-3 ag and 12 h for 3 ah-3 aq.

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Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Cited by 100 publications

References 41 publications

Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination

Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination

Boron in Heat‐Treatable Steels: A Review

Copper‐Catalyzed Intermolecular Hydroamination of Arylamines or Aza‐Heterocycles with Nitrostyrene Derivatives

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Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Cited by 100 publications

References 41 publications

Reactions of Diethylamine and Ethylene Catalyzed by PtII or Pt0 – Transalkylation vs. Hydroamination

Reactions of Diethylamine and Ethylene Catalyzed by PtII or Pt0 – Transalkylation vs. Hydroamination

Boron in Heat‐Treatable Steels: A Review

Copper‐Catalyzed Intermolecular Hydroamination of Arylamines or Aza‐Heterocycles with Nitrostyrene Derivatives

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Product

Resources

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Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination

Reactions of Diethylamine and Ethylene Catalyzed by Pt^II or Pt⁰ – Transalkylation vs. Hydroamination