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Allylic Amination (allylic + amination)
Selected AbstractsAllylic Amination of Internal Alkynes with Aromatic and Aliphatic Amines Using Polymer-Supported Triphenylphosphane,Palladium Complex as a Heterogeneous and Recyclable CatalystEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 26 2010Yogesh S. Wagh Abstract A facile and novel protocol for the allylic amination of internal alkynes with amines by using a polymer-supported triphenylphosphane,palladium complex [PS,TPP,Pd] as a highly active heterogeneous reusable catalyst was developed. The catalyst exhibited remarkable activity and is reusable over five consecutive cycles. The protocol was applicable for a variety of hindered and functionalized aromatic/aliphatic amines and afforded the desired allylic products in good to excellent yield. [source] Towards Continuous Flow, Highly Enantioselective Allylic Amination: Ligand Design, Optimization and SupportingADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 10 2009Dana Popa Abstract A family of enantiopure diphenylphosphinooxazolines (PHOX) containing in their structures a sterically tunable alkoxymethyl group (-CH2OR) has been optimized for the palladium-catalyzed asymmetric allylic amination. The optimal catalyst (R=CH3), depicting very high catalytic activity and broad scope applicability, has been further modified to include an ,-alkynyloxy substituent of variable length for polymer supporting via click chemistry, and has been anchored onto slightly cross-linked azidomethyl poly(styrene). The length of a polymethylene chain connecting the PHOX unit with the 1,2,3-triazole linker has been optimized, and the first polymer-supported PHOX ligands for the highly enantioselective allylic amination have been prepared in this manner. Conditions for catalyst recovery and reuse in microwave-promoted amination reactions have been established, and the system has been finally adapted to continuous flow operation. [source] ChemInform Abstract: Enantioselecitve Iridium-Catalyzed Allylic Amination of Ammonia and Convenient Ammonia Surrogates.CHEMINFORM, Issue 12 2008Mark J. Pouy Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates.CHEMINFORM, Issue 48 2007Barry M. Trost Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] Allylic Amination of Unfunctionalyzed Olefins by Nitroarenes and CO, Catalyzed by Ru3(CO)12/Ph-BIAN (Ph-BIAN = Bis(phenylimino)acenaphthenequinone): Extension to the Synthesis of Allylic Amines with Strongly Electron-Withdrawing or Electron-Donating Groups on the Aryl Ring.CHEMINFORM, Issue 38 2004Fabio Ragaini Abstract For Abstract see ChemInform Abstract in Full Text. [source] Identification of an Activated Catalyst in the Iridium-Catalyzed Allylic Amination and Etherification.CHEMINFORM, Issue 12 2004Increased Rates, Scope, Selectivity. Abstract For Abstract see ChemInform Abstract in Full Text. [source] ChemInform Abstract: Asymmetric Catalysis of Planar-Chiral Cyclopentadienylruthenium Complexes in Allylic Amination and Alkylation.CHEMINFORM, Issue 7 2002Yuji Matsushima Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] Enantioselective Synthesis of 3-Azabicyclo[4.1.0]heptenes and 3-Azabicyclo[3.2.0]heptenes by Ir-Catalyzed Asymmetric Allylic Amination of N -Tosyl Propynylamine and Pt-Catalyzed CycloisomerizationCHEMISTRY - A EUROPEAN JOURNAL, Issue 22 2010Ji-Bao Xia Irresistible! Highly regio- and enantioselective Ir-catalyzed allylic amination reactions of N -tosyl propynylamines have been realized. The resulting N -tosyl allylpropynylamines were transformed into highly enantioenriched 3-azabicyclo[4.1.0]heptenes and 3-azabicyclo[3.2.0]heptenes, respectively, in the presence of PtCl2 (see scheme; Ts=tosyl, cod=1,5-cyclooctadiene, TBAF=tetrabutylammonium fluoride, TMS=trimethylsilyl). [source] Allylic Amination of Internal Alkynes with Aromatic and Aliphatic Amines Using Polymer-Supported Triphenylphosphane,Palladium Complex as a Heterogeneous and Recyclable CatalystEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 26 2010Yogesh S. Wagh Abstract A facile and novel protocol for the allylic amination of internal alkynes with amines by using a polymer-supported triphenylphosphane,palladium complex [PS,TPP,Pd] as a highly active heterogeneous reusable catalyst was developed. The catalyst exhibited remarkable activity and is reusable over five consecutive cycles. The protocol was applicable for a variety of hindered and functionalized aromatic/aliphatic amines and afforded the desired allylic products in good to excellent yield. [source] Towards Continuous Flow, Highly Enantioselective Allylic Amination: Ligand Design, Optimization and SupportingADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 10 2009Dana Popa Abstract A family of enantiopure diphenylphosphinooxazolines (PHOX) containing in their structures a sterically tunable alkoxymethyl group (-CH2OR) has been optimized for the palladium-catalyzed asymmetric allylic amination. The optimal catalyst (R=CH3), depicting very high catalytic activity and broad scope applicability, has been further modified to include an ,-alkynyloxy substituent of variable length for polymer supporting via click chemistry, and has been anchored onto slightly cross-linked azidomethyl poly(styrene). The length of a polymethylene chain connecting the PHOX unit with the 1,2,3-triazole linker has been optimized, and the first polymer-supported PHOX ligands for the highly enantioselective allylic amination have been prepared in this manner. Conditions for catalyst recovery and reuse in microwave-promoted amination reactions have been established, and the system has been finally adapted to continuous flow operation. [source] Diphosphines of dppf-Type Incorporating Electron-Withdrawing Furyl Moieties Substantially Improve the Palladium-Catalysed Amination of Allyl AcetatesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 9 2005Aziz Fihri Abstract Highly active Pd/diphosphine catalytic systems incorporating new, air-stable ferrocenyl-furylphosphines allow nucleophilic allylic amination at room temperature with unprecedented turnover frequencies. For instance, in the presence of 0.01,mol,% catalyst the coupling of aniline to allyl acetate occurs at a TOF of more than 10,000,h,1; even the addition of the less nucleophile morpholine to allyl acetate is observed with a TOF of 4250,h,1. The amination of the sterically demanding geranyl acetate, a monoterpene derivative of interest in the flavour industry, at low catalyst loadings demonstrates the scope of this methodology, which provides in addition noticeable advantages in terms of economical (resource- and energy-saving) and sustainable chemistry (high selectivity, no additive, low metal content, and thus easier purification). [source] Efficient palladium,ferrocenylphosphine catalytic systems for allylic amination of monoterpene derivativesAPPLIED ORGANOMETALLIC CHEMISTRY, Issue 12 2006Duc Hanh Nguyen Abstract Ferrocenylphosphines added to [Pd(µ-Cl)(,3 -C3H5)]2 dimeric precursor produce efficient catalysts to effect the allylic amination of terpenic allylacetates. Particularly convenient are tetrakis(diphenylphosphino)ferrocene and 1,1,-bis(diphenylphosphino)ferrocene, which allow the amination of allylacetates with good to excellent selectivity, and have turnover numbers as high as 80 000, for instance, for the formation of allylaniline. Herein, we report on reactions that selectively transform geranylacetate, nerylacetate, linalylacetate and perillylacetate into the corresponding allylic amines. These preparative methods give facile access to various products of great potential industrial interest. Copyright © 2006 John Wiley & Sons, Ltd. [source] ChemInform Abstract: Catalytic Asymmetric Synthesis of 2,5-Naphthylpyrrolidine.CHEMINFORM, Issue 32 2010Johannes F. Teichert Abstract Based on an Ir-catalyzed double allylic amination with ammonia, the chiral title compound (VI) is prepared. [source] | ||||||||||