- A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
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The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.
- Zelenay, Benjamin,Munton, Peter,Tian, Xiaojie,Díez-González, Silvia
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supporting information
p. 4725 - 4730
(2019/08/01)
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- An unprecedented tandem annulation of ω-azido-1-alkynes with diaryl-iodonium salts: A facile synthesis of polycyclic quinolines
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Polysubstituted quinolines are synthesized through an unprecedented cascade annulation of ω-azido-1-alkynes with diaryliodonium salts, which serve as C2-building blocks. The reaction proceeds smoothly and is catalyzed by Cu(I) catalysts to give various qu
- Chen, Junjie,Chen, Chao,Chen, Jing,Gao, Hongpeng,Qu, Hongmei
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p. 2721 - 2726
(2015/01/08)
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- The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles
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The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo[3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo[3,4-
- Page, Lee W.,Bailey, Matthew,Beswick, Paul J.,Frydrych, Simon,Gleave, Robert J.
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scheme or table
p. 3388 - 3391
(2010/09/05)
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- Constrained geometry organoactinides as versatile catalysts for the intramolecular hydroamination/cyclization of primary and secondary amines having diverse tethered C-C unsaturation
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A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)2 (CGC = Me2-Si(η5-Me 4C5)(tBuN); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl2, 2-Cl2) and slightly more soluble diiodides (1-I2, 2-I2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp″ 2AnR2 (Cp″ = η5-Me4C 5; An = Th, R = CH2-(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp′2AnR2 (Cp′ = η5-Me5C5 ; An = Th, R = CH 2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N t up to 3000 h-1) and high regioselectivities (≥95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting C=C/C=C insertion into the An-N σ-bond.
- Stubbert, Bryan D.,Marks, Tobin J.
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p. 4253 - 4271
(2008/02/01)
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- Intramolecular hydroamination of alkynes catalyzed by Pd(PPh 3)4/triphenylphosphine under neutral conditions
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The intramolecular hydroamination of alkynes tethered with amino group 1 in the presence of catalytic amounts of Pd(PPh3)4 and PPh3 in benzene at 100°C proceeded smoothly without the use of any additional acid source to af
- Bajracharya, Gan B.,Huo, Zhibao,Yamamoto, Yoshinori
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p. 4883 - 4886
(2007/10/03)
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- Palladium-Catalyzed Intramolecular Addition of Amines to Acetylenes. Synthesis of Cyclic Imines
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Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines.Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-
- Fukuda, Yukitoshi,Matsubara, Seijiro,Utimoto, Kiitiro
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p. 5812 - 5816
(2007/10/02)
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- Preparation of 2,3,4,5-tetrahydropyridines from 5-alkynylamines under the catalytic action of gold(III) salts
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Intramolecular addition of amine to carbon-carbon triple bonds in 5-alkynylamines produces 2,3,4,5-tetrahydropyridines under the catalytic action of an aurate salt. Some venom components of various ant species are synthesized by the application of this re
- Fukuda,Utimoto
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p. 975 - 978
(2007/10/02)
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