Palladium‐Catalyzed Highly Regioselective Mizoroki–Heck Arylation of Allylamines with Aryl Chlorides

No abstract is available for this paper.

• Publication year

  2014

• Venue

  ChemCatChem

• Publication date

  2014-01-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1002/cctc.201300755
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Selective arylation and vinylation at the α position of vinylarenes.

  2013cited by this paper
• Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

  2012cited by this paper
• Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage.

  2012cited by this paper
• Palladium-Catalyzed Highly Regioselective and Stereoselective Arylation of Electron-Rich Allylamines with Aryl Bromides.

  2012cited by this paper
• Intermolecular Mizoroki-Heck reaction of aliphatic olefins with high selectivity for substitution at the internal position.

  2012cited by this paper
• Palladium‐Catalyzed, Highly Efficient, Regiocontrolled Arylation of Electron‐Rich Allylamines with Aryl Halides

  2012cited by this paper
• Palladium‐Catalyzed, Chelation‐Assisted Stereo‐ and Regioselective Synthesis of Tetrasubstituted Olefins by Oxidative Heck Arylation

  2012cited by this paper
• Palladium-Catalyzed Highly Regioselective Arylation of Allylamines with Thiophenes and Furans

  2012cited by this paper
• Double arylation of allyl alcohol via a one-pot Heck arylation-isomerization-acylation cascade.

  2011cited by this paper
• Convenient synthesis of (E)-5-aminoallyl-2'-deoxycytidine and some related derivatives

  2011cited by this paper
• The asymmetric Heck and related reactions.

  2011cited by this paper
• From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction.

  2011cited by this paper
• Copper-catalyzed intramolecular dehydrogenative aminooxygenation: direct access to formyl-substituted aromatic N-heterocycles.

  2011cited by this paper
• An efficient and general method for the Heck and Buchwald-Hartwig coupling reactions of aryl chlorides.

  2011cited by this paper
• Allylic C-H alkylation of unactivated α-olefins: serial ligand catalysis resumed.

  2011cited by this paper
• An improved Larock synthesis of quinolines via a Heck reaction of 2-bromoanilines and allylic alcohols.

  2011cited by this paper
• C-N bond cleavage of allylic amines via hydrogen bond activation with alcohol solvents in Pd-catalyzed allylic alkylation of carbonyl compounds.

  2011cited by this paper
• Recent advances in the Heck–Matsuda reaction in heterocyclic chemistry

  2011cited by this paper
• Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins.

  2011cited by this paper
• Substrate-directable Heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines.

  2011cited by this paper
• Palladium-catalyzed Heck reaction of aryl chlorides under mild conditions promoted by organic ionic bases.

  2011cited by this paper
• Chelation-assisted palladium-catalyzed high regioselective heck diarylation reaction of 9-allyl-9H-purine: synthesis of 9-(3,3-diaryl-allyl)-9H-purines

  2011cited by this paper
• Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles.

  2011cited by this paper
• Evolution And Synthetic Applications Of The Heck-matsuda Reaction: The Return Of Arenediazonium Salts To Prominence

  2011cited by this paper
• Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.

  2010cited by this paper
• Tetraalkylammonium-free heck olefination of deactivated chloroarenes by using a macrocyclic catalyst precursor.

  2010cited by this paper
• Catalytic asymmetric allylic alkylation employing heteroatom nucleophiles: a powerful method for C–X bond formation

  2010cited by this paper
• A novel approach to 3-methylindoles by a Heck/cyclization/isomerization process.

  2010cited by this paper
• Pd(II)-catalyzed highly selective arylation of allyl esters via C-H functionalization of unreactive arenes with retention of the traditional leaving group.

  2010cited by this paper
• Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids.

  2010cited by this paper
• Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides.

  2010cited by this paper
• Heck reactions with palladium nanoparticles in ionic liquids: coupling of aryl chlorides with deactivated olefins.

  2009cited by this paper
• Palladium(II)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction.

  2009cited by this paper
• The Mizoroki–Heck Reaction

  2009cited by this paper
• Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters.

  2009cited by this paper
• N4-tetradentate dicarboxyamidate/dipyridyl palladium complexes as robust catalysts for the Heck reaction of deactivated aryl chlorides.

  2009cited by this paper
• Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries

  2009cited by this paper
• 4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides

  2009cited by this paper
• Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group.

  2008cited by this paper
• Palladaphosphacyclobutenes as catalysts in Heck and Suzuki reactions

  2008cited by this paper
• Metal-catalyzed enantioselective allylation in asymmetric synthesis.

  2008cited by this paper
• Regioselective Heck Reaction of N‐Vinylphthalimide: A General Strategy for the Synthesis of (E)‐N‐Styrylphthalimides and Phenethylamines

  2008cited by this paper
• A general and highly selective chelate-controlled intermolecular oxidative Heck reaction.

  2008cited by this paper
• The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands.

  2008cited by this paper
• Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides.

  2008cited by this paper
• Metallkatalysierte enantioselektive Allylierungen in der asymmetrischen Synthese

  2008cited by this paper
• The Heck-Mizoroki cross-coupling reaction: a mechanistic perspective.

  2007cited by this paper
• Pd(II) complexes of a sterically bulky, benzannulated N-heterocyclic carbene and their catalytic activities in the Mizoroki–Heck reaction

  2007cited by this paper
• Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water.

  2007cited by this paper
• Arylation of Allyl Alcohols in Organic and Aqueous Media Catalyzed by Oxime-Derived Palladacycles : Synthesis of β-Arylated Carbonyl Compounds

  2007cited by this paper
• Rate and Mechanism of the Heck Reactions of Arylpalladium Complexes Ligated by a Bidentate P,P Ligand with an Electron-Rich Alkene (Isobutyl Vinyl Ether)

  2007cited by this paper
• Highly Functionalised Sulfur-Based Silica Scavengers for the Efficient Removal of Palladium Species from Active Pharmaceutical Ingredients

  2007cited by this paper
• Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate P,P ligand in Heck reactions.

  2007cited by this paper
• The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors.

  2006cited by this paper
• Regioselective Heck arylation of unsaturated alcohols by palladium catalysis in ionic liquid.

  2006cited by this paper
• On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review

  2006cited by this paper
• Selective terminal heck arylation of vinyl ethers with aryl chlorides: a combined experimental-computational approach including synthesis of betaxolol.

  2006cited by this paper
• An efficient palladium-catalyzed Heck coupling of aryl chlorides with alkenes

  2006cited by this paper
• Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714

  2005cited by this paper
• Tetrahedron report number 714 Palladium-catalysed reactions of alcohols. Part B: Formation of C-C and C-N bonds from unsaturated alcohols

  2005cited by this paper
• Neighbouring‐Group Effects in Heck Reactions

  2005cited by this paper
• Ionic liquid-promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides.

  2005cited by this paper
• Palladium-catalyzed cross-coupling reactions in total synthesis.

  2005cited by this paper
• Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese

  2005cited by this paper
• Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction

  2005cited by this paper
• The development of palladium catalysts for CC and Cheteroatom bond forming reactions of aryl chloride substrates

  2004cited by this paper
• Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane.

  2004cited by this paper
• High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

  2004cited by this paper
• Industrial R&D on Catalytic CC and CN Coupling Reactions: A Personal Account on Goals, Approaches and Results

  2004cited by this paper
• Chelation-Induced Catalytic Multiple Arylation of Allylic 2-Pyridyl Sulfones

  2004cited by this paper
• Recent advances in the Baylis-Hillman reaction and applications.

  2003cited by this paper
• Characterization of a series of 3-amino-2-phenylpropene derivatives as novel bovine chromaffin vesicular monoamine transporter inhibitors.

  2003cited by this paper
• Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air.

  2003cited by this paper
• Palladium-catalyzed cross-coupling reaction of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide

  2003cited by this paper
• Pd nanoparticles catalyzed stereospecific synthesis of beta-aryl cinnamic esters in ionic liquids.

  2003cited by this paper
• Fine Chemical Synthesis with Homogeneous Palladium Catalysts: Examples, Status and Trends

  2002cited by this paper
• New palladium carbene catalysts for the Heck reaction of aryl chlorides in ionic liquids.

  2002cited by this paper
• First Application of Secondary Phosphines as Supporting Ligands for the Palladium‐Catalyzed Heck Reaction: Efficient Activation of Aryl Chlorides

  2002cited by this paper
• Palladiumkatalysierte Kupplungen von Arylchloriden

  2002cited by this paper
• Direct Coupling of Oxazolines and N-Heterocyclic Carbenes: A Modular Approach to a New Class of C−N Donor Ligands for Homogeneous Catalysis

  2002cited by this paper
• Palladium-catalyzed coupling reactions of aryl chlorides.

  2002cited by this paper
• β-Regioselective intermolecular Heck arylation of N,N-disubstituted allylamines

  2001cited by this paper
• Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.

  2001cited by this paper
• A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions.

  2001cited by this paper
• A Pd complex of a tridentate pincer CNC bis-carbene ligand as a robust homogenous Heck catalyst

  2001cited by this paper
• Advances in the Heck Chemistry of Aryl Bromides and Chlorides

  2001cited by this paper
• Unusual Palladium-Catalyzed Cascade Arylation ofα,β-Unsaturated Phenyl Sulfones under Heck Reaction Conditions

  2001cited by this paper
• The Heck reaction in the production of fine chemicals

  2001cited by this paper
• Acetylferrocenyloxime palladacycle-catalyzed Heck reactions

  2001cited by this paper
• Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination.

  2001cited by this paper
• Heck reaction catalyzed by PD-modified zeolites.

  2001cited by this paper
• Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides.

  2001cited by this paper
• Thermal stability of cis-dithiocyanato(2,2′-bipyridyl4,4′dicarboxylate) ruthenium(II) photosensitizer in the free form and on nanocrystalline TiO2 films

  2000cited by this paper
• Donor-Functionalized Heterocyclic Carbene Complexes of Palladium(II): Efficient Catalysts for C−C Coupling Reactions

  2000cited by this paper
• Palladium-catalyzed intermolecular coupling of aryl halides and amides.

  2000cited by this paper
• Highly regioselective palladium-catalyzed beta-arylation of N, N-dialkylallylamines

  2000cited by this paper
• Aryl–Pd covalently bonded palladacycles, novel amino and oxime catalysts {di-μ-chlorobis(benzaldehydeoxime-6-C,N)dipalladium(II), di-μ-chlorobis(dimethylbenzylamine-6-C,N)dipalladium(II)} for the Heck reaction☆

  2000cited by this paper
• Heck reaction in ionic liquids catalyzed by a Pd–benzothiazole carbene complex

  2000cited by this paper
• Polymer-supported carbene complexes of palladium: well-defined, air-stable, recyclable catalysts for the Heck reaction

  2000cited by this paper
• Nonaqueous ionic liquids: superior reaction media for the catalytic Heck-vinylation of chloroarenes

  2000cited by this paper

• Palladium-Catalyzed Decarboxylative C─H Alkenylation of Proaromatic Acids With Allyl Alcohols and N-Allyl Sulfonamides.

  2026cites this paper
• Ionic Liquids in Metal, Photo-, Electro-, and (Bio) Catalysis.

  2024cites this paper
• Scalable Synthesis of Cinnamylamines Via the Heck Reaction: Application in the Synthesis of Abamine, Naftifine and Reboxetine

  2024cites this paper
• Controlling Reactivity and Selectivity in the Mizoroki-Heck Reaction: High Throughput Evaluation of 1,5-Diaza-3,7-diphosphacyclooctane Ligands.

  2024cites this paper
• Formation and stabilization of nanosized Pd particles in catalytic systems: Ionic nitrogen compounds as catalytic promoters and stabilizers of nanoparticles

  2021cites this paper
• Rhodium(III)‐Catalyzed Selective Direct Olefination of Imidazoles

  2018cites this paper
• Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

  2018cites this paper
• Rhodium(I)-catalysed decarbonylative direct C–H vinylation and dienylation of arenes

  2018cites this paper
• Combining Copper‐Catalyzed Hydroboration with Palladium‐Catalyzed Suzuki Coupling for the One‐pot Synthesis of Arylallylamines under Micellar Conditions

  2017cites this paper
• Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines.

  2017cites this paper
• Palladium-catalyzed highly regioselective and stereoselective decarboxylative arylation of unactivated olefins with aryl carboxylic acids

  2017cites this paper
• Rhodium(III)‐Catalyzed Direct CH Olefination of Arenes with Aliphatic Olefins

  2016cites this paper
• Intramolecular oxyacetoxylation of N-allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride-pyridine system.

  2016cites this paper
• Palladium‐Catalyzed Direct Arylation of Allylamines with Simple Arenes

  2015cites this paper