Cart
Communication
Ruthenium-Catalyzed Intramolecular Oxidative Amination of Aminoalkenes Enables Rapid Synthesis of Cyclic Imines
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
[RuCl2(CO)3]2/dppp is shown to be a highly effective catalyst system for the first intramolecular oxidative amination of a variety of aminoalkenes when it is used concomitantly with K2CO3 and allyl acetate in N-methylpiperidine, to give the corresponding cyclic imines and indoles in excellent yields. For example, the reaction of 2,2-diphenyl-4-pentenyl-1-amine performed in the presence of 2 mol % of [RuCl2(CO)3]2, 4 mol % of dppp, K2CO3, and allyl acetate in N-methylpiperidine at 140 °C for 8 h gives 4,4-diphenyl-2-methyl-1-pyrroline in quantitative (>99%) yield.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 19 ACS Journal articles (5 most recent appear below).
New Rhodium(I) and Iridium(I) Complexes Containing Mixed Pyrazolyl–1,2,3-Triazolyl Ligands As Catalysts for Hydroamination
Carol Hua, Khuong Q. Vuong, Mohan Bhadbhade, and Barbara A. MesserleOrganometallics2012 Article ASAPNew Rhodium(I) and Iridium(I) Complexes Containing Mixed Pyrazolyl–1,2,3-Triazolyl Ligands As Catalysts for Hydroamination
Carol Hua, Khuong Q. Vuong, Mohan Bhadbhade, and Barbara A. MesserleOrganometallics2012 Article ASAPTwo new bidentate pyrazolyl–triazolyl donor ligands, 4-((1H-pyrazol-1-yl)methyl)-1-benzyl-1H-1,2,3-triazole, PyT (1a), and 4-((1H-pyrazol-1-yl)methyl)-1-phenyl-1H-1,2,3-triazole, PyS (1b), were synthesized using the copper(I)-catalyzed “click” reaction ...
Heavier Alkaline Earth Catalysts for the Intermolecular Hydroamination of Vinylarenes, Dienes, and Alkynes
Christine Brinkmann, Anthony G. M. Barrett, Michael S. Hill, and Panayiotis A. ProcopiouJournal of the American Chemical Society2012 134 (4), 2193-2207Heavier Alkaline Earth Catalysts for the Intermolecular Hydroamination of Vinylarenes, Dienes, and Alkynes
Christine Brinkmann, Anthony G. M. Barrett, Michael S. Hill, and Panayiotis A. ProcopiouJournal of the American Chemical Society2012 134 (4), 2193-2207The heavier group 2 complexes [M{N(SiMe3)2}2]2(1, M = Ca; 2, M = Sr) and [M{CH(SiMe3)2}2(THF)2] (3, M = Ca; 4, M = Sr) are shown to be effective precatalysts for the intermolecular hydroamination of vinyl arenes and dienes under mild conditions. Initial ...
Catalytic, Enantioselective Intramolecular Hydroamination of Primary Amines Tethered to Di- and Trisubstituted Alkenes
Yulia Chapurina, Houssein Ibrahim, Régis Guillot, Emilie Kolodziej, Jacqueline Collin, Alexander Trifonov, Emmanuelle Schulz, and Jérôme HannedoucheThe Journal of Organic Chemistry2011 76 (24), 10163-10172Catalytic, Enantioselective Intramolecular Hydroamination of Primary Amines Tethered to Di- and Trisubstituted Alkenes
Yulia Chapurina, Houssein Ibrahim, Régis Guillot, Emilie Kolodziej, Jacqueline Collin, Alexander Trifonov, Emmanuelle Schulz, and Jérôme HannedoucheThe Journal of Organic Chemistry2011 76 (24), 10163-10172The in situ preparation of chiral amido alkyl ate yttrium complexes from an array of chiral N-benzyl-like-substituted binaphthyldiamines is reported. These chiral heteroleptic complexes are shown to be efficient catalysts for the enantioselective ...
Intramolecular Aminoalkene Hydroamination Catalyzed by Magnesium Complexes Containing Multidentate Phenoxyamine Ligands
Xiaoming Zhang, Thomas J. Emge, and Kai C. HultzschOrganometallics2010 29 (22), 5871-5877Intramolecular Aminoalkene Hydroamination Catalyzed by Magnesium Complexes Containing Multidentate Phenoxyamine Ligands
Xiaoming Zhang, Thomas J. Emge, and Kai C. HultzschOrganometallics2010 29 (22), 5871-5877The magnesium complexes L2MgiPr (L2 = 4-tert-butyl-6-(triphenylsilyl)-2-[bis((3-(dimethylamino)propyl)amino)methyl]phenoxyl) and L3MgiPr (L3 = 4-tert-butyl-6-(triphenylsilyl)-2-[benzyl((3-(dimethylamino)propyl)amino)methyl]phenoxyl) supported by ...
Platinum-Catalyzed, One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization
Noriko Okamoto, Kei Takeda, and Reiko YanadaThe Journal of Organic Chemistry2010 75 (22), 7615-7625Platinum-Catalyzed, One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization
Noriko Okamoto, Kei Takeda, and Reiko YanadaThe Journal of Organic Chemistry2010 75 (22), 7615-7625By using platinum(II) chloride as a Lewis acid catalyst, concise and efficient syntheses of indole carbamates, 1,2-dihydroisoquinoline carbamates, macrocyclic indole carbamates, indole ureas, and indole phosphoranes have been achieved via tandem Hofmann-...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue January 16, 2002
- Received September 6, 2001
Revised November 12, 2001
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
CH2)]2 (2.5 mol %) and PPh3 in dioxane at 120 °C for 16 h led to isolation of 1-benzyl-2-methyl-4,4-diphenylpyrrolidine in 75% yield. A number of γ- and δ-amino ...
