Allenes and computational chemistry: from bonding situations to reaction mechanisms
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Title
Allenes and computational chemistry: from bonding situations to reaction mechanisms
Authors
Keywords
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Journal
CHEMICAL SOCIETY REVIEWS
Volume 43, Issue 9, Pages 3041
Publisher
Royal Society of Chemistry (RSC)
Online
2014-02-20
DOI
10.1039/c3cs60457h
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- Computation-Guided Development of Au-Catalyzed Cycloisomerizations Proceeding via 1,2-Si or 1,2-H Migrations: Regiodivergent Synthesis of Silylfurans
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- Phosphine-Catalyzed Formation of Carbon−Sulfur Bonds: Catalytic Asymmetric Synthesis of γ-Thioesters
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- Mechanistic Study of Gold(I)-Catalyzed Intermolecular Hydroamination of Allenes
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- Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers
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- A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes
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- Allenamide Hydro−Hydroxyalkylation: 1,2-Amino Alcohols via Ruthenium-Catalyzed Carbonylanti-Aminoallylation
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- Platinum-Catalyzed Intramolecular Hydroarylation of Allenyl Arenes: Efficient Synthesis of 1,4-Dihydronaphthalenes
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- Stereoselective 6π-Electron Electrocyclic Ring Closures of 2-Halo-Amidotrienes via a Remote 1,6-Asymmetric Induction
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- Regioselective Synthesis oftert-Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes
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- Palladium-Catalyzed [3,3]-Rearrangement for the Facile Synthesis of Allenamides
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- Highly Selective Cobalt-Mediated [6 + 2] Cycloaddition of Cycloheptatriene and Allenes
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- C−H Bond Activation Reactions in π-Allene−Osmium−Triisopropylphosphine Complexes with Cyclopentadienyl or Hydridotris(pyrazolyl)borate Ligands: Formation of Isopropenyldiisopropylphosphine versus Hydride−Alkenylcarbyne Derivatives
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- C−H Bond Activation of Terminal Allenes: Formation of Hydride-Alkenylcarbyne-Osmium and Disubstituted Vinylidene-Ruthenium Derivatives∥
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- From Allenes to Edge-Bridging Allyl Ligands or Face-Capping Alkenyl Ligands on a Triruthenium Hydrido Carbonyl Cluster: An Experimental and DFT Computational Study†
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- Solid-State and Dynamic Solution Behavior of a Cationic, Two-Coordinate Gold(I) π-Allene Complex
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- Transition-metal-catalyzed cleavage of carbon–selenium bond and addition to alkynes and allenes
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- Mechanistic elucidation of ketenimine–butynoate cycloaddition reaction: role of biradical intermediates in isotopomeric purity of benzyl (1,1a,6,6a-13C4)-6-methyl anthranilic ester
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- Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides
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- Studies on the asymmetric, phosphine-promoted [3+2] annulations of allenic esters with 2-aryl-1,1-dicyanoalkenes
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- Electrophilic Addition and Cyclization Reactions of Allenes
- (2009) Shengming Ma ACCOUNTS OF CHEMICAL RESEARCH
- Tandem Enzyme/Gold-Catalysis: From Racemic α-Allenic Acetates to Enantiomerically Enriched 2,5-Dihydrofurans in One Pot
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- Synthesis of Chiral 2-Phospha[3]ferrocenophanes and their Behaviour as Organocatalysts in [3+2] Cyclization Reactions
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- Ferric Chloride Hexahydrate-Catalyzed Highly Regio- and Stereoselective Conjugate Addition Reaction of 2,3-Allenoates with Grignard Reagents: An Efficient Synthesis of β,γ-Alkenoates
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- N-Heterocyclic Carbene Gold(I) Catalyzed Transformation of N-Tethered 1,5-Bisallenes to 6,7-Dimethylene-3-azabicyclo[3.1.1]heptanes
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- Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles
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- Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium-Catalyzed CC Bond-Forming Transfer Hydrogenation
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- Stable Five-Membered-Ring Allenes with Second-Row Elements Only: Not Allenes, But Zwitterions
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- Are Allenes with Zwitterionic Character Still Allenes? Of Course!
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- Synthesis and Ligand Properties of a Persistent, All-Carbon Four-Membered-Ring Allene
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- Mechanistic Surprises in the Gold(I)-Catalyzed Intramolecular Hydroarylation of Allenes
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- The Role of Water in Platinum-Catalyzed Cycloisomerization of 1,6-Enynes: A Combined Experimental and Theoretical Gas Phase Study
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- Unusual regiodivergence in metal-catalysed intramolecular cyclisation of γ-allenols
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- Dyotropic Reactions: Mechanisms and Synthetic Applications†
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- Exploiting [2+2] cycloaddition chemistry: achievements with allenes
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- Do Extremely Bent Allenes Exist?
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- Double Group Transfer Reactions: Role of Activation Strain and Aromaticity in Reaction Barriers
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- Gold-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Aryl-1-allene-6-enes
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- Regioselectivity Control in the Metal-Catalyzed Functionalization of γ-Allenols, Part 2: Theoretical Study
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- Regioselectivity Control in the Metal-Catalyzed OC Functionalization of γ-Allenols, Part 1: Experimental Study
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- Gold-Catalyzed [4C+3C] Intramolecular Cycloaddition of Allenedienes: Synthetic Potential and Mechanistic Implications
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- Cyclization of Propargylic Amides: Mild Access to Oxazole Derivatives
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- Expanding the Scope of Enantioselective FerroPHANE-Promoted [3+2] Annulations with α,β-Unsaturated Ketones
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- Divalent Silicon(0) Compounds
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- Divalent E(0) Compounds (E=Si-Sn)
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- Reactions of Cationic Gold(I) with Allenoates: Synthesis of Stable Organogold(I) Complexes and Mechanistic Investigations on Gold-Catalyzed Cyclizations
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- Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence
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- A Decade of Advancements in Pauson-Khand-Type Reactions
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- An Experimental and Theoretical Study on the Interaction ofN-Heterocyclic Carbene-Derived 1,3-Dipoles with Methoxycarbonylallenes: Highly Regio- and Stereoselective [3+2]-Cycloadditions Controlled by the Structures ofN-Heterocycles of 1,3-Dipoles
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- Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole Synthesis through Indolidene Intermediates
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- Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis
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- Platinum(II)-Catalyzed Intermolecular [3 + 2] Cycloaddition of Propadienyl Silyl Ethers and Alkenyl Ethers
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- Exocyclic Delocalization at the Expense of Aromaticity in 3,5-bis(π-Donor) Substituted Pyrazolium Ions and Corresponding Cyclic Bent Allenes†
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- Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor
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- Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives
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- Mechanistic Studies on Au(I)-Catalyzed [3,3]-Sigmatropic Rearrangements using Cyclopropane Probes
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- Generation and Trapping of Cyclopentenylidene Gold Species: Four Pathways to Polycyclic Compounds
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- Stereoselective Synthesis of γ-Substituted (Z)-Allylic Boranes via Kinetically Controlled Hydroboration of Allenes with 10-TMS-9-borabicyclo[3.3.2]decane
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- Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways
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- Allenes in Asymmetric Catalysis: Asymmetric Ring Opening ofmeso-Epoxides Catalyzed by Allene-Containing Phosphine Oxides
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- Enantioselective Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones by Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Allenes
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- Möbius aromaticity and antiaromaticity in expanded porphyrins
- (2009) Zin Seok Yoon et al. Nature Chemistry
- Coordination chemistry at carbon
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- Rethinking carbon
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- Creative approaches towards the synthesis of 2,5-dihydro- furans, thiophenes, and pyrroles. One method does not fit all!
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- Origin of Thermodynamic versus Kinetic Control of Allene Hydroboration with 9-Borabicyclo[3.3.1]nonane and 10(R)-Trimethylsilyl-9-Borabicyclo[3.3.2]decane
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- Rhodium-Mediated Enantioselective Cyclopropanation of Allenes
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- Ketonitrones via Cope-Type Hydroamination of Allenes
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- Copper-CatalyzedN-Allenylation of Allylic Sulfonamides
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- Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes: A DFT study
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- On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions
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- Regioselective Bis-Selenation of Allenes Catalyzed by Palladium Complexes: A Theoretical Study
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- Carbopalladation of Maleate and Fumarate Esters and 1,1-Dimethylallene with Ortho-Substituted Aryl Palladium Complexes
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- Divalent carbon atom as the proton acceptor in hydrogen bonding
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- Divalent carbon(0) compounds
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- Intermolecular rhodium catalyzed hydroacylation of allenes: the regioselective synthesis of β,γ-unsaturated ketones
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- Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes†
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- Highly Regio- and Stereoselective Double Michael Addition-Cyclization of 2,3-Allenoates with Organozinc Compounds: Efficient Synthesis of 5-Benzylidenecyclohex-2-enones
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- Carbodicarbenes: Divalent Carbon(0) Compounds
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- The Role of Bent Acyclic Allene Gold Complexes in Axis-to-Center Chirality Transfers
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- Coordination Chemistry of Ene-1,1-diamines and a Prototype “Carbodicarbene”
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- Synthesis of an Extremely Bent Acyclic Allene (A “Carbodicarbene”): A Strong Donor Ligand
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- Golden Opportunities in Stereoselective Catalysis
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- Transition metal-catalyzed three-component coupling of allenes and the related allylation reactions
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- Mechanism of the Palladium-Catalyzed Carbohydroxylation of Allene-Substituted Conjugated Dienes: Rationalization of the Recently Observed Nucleophilic Attack by Water on a (π-Allyl)palladium Intermediate
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- Is an MN σ-Bond Insertion Route a Viable Alternative to the MN [2+2] Cycloaddition Route in Intramolecular Aminoallene Hydroamination/Cyclisation Catalysed by Neutral Zirconium Bis(amido) Complexes? A Computational Mechanistic Study
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- Chemodivergence in Alkene/Allene Cycloetherification of Enallenols: Iron versus Noble Metal Catalysis
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- Mechanism, Regioselectivity, and the Kinetics of Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Allenoates and Electron-Deficient Alkenes
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- Divalent Carbon(0) Chemistry, Part 1: Parent Compounds
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- Frontside versus Backside SN2 Substitution at Group 14 Atoms: Origin of Reaction Barriers and Reasons for Their Absence
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- Chemistry of Energetically Activated Cumulenes—From Allene (H2CCCH2) to Hexapentaene (H2CCCCCCH2)
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- Carbon-Centered Radical Addition and β-Scission Reactions: Modeling of Activation Energies and Pre-exponential Factors
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- Insertion reactions of allenes with transition metal complexes
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- Reaction mechanism of palladium-catalyzed silastannation of allenes by density functional theory
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- Stereoselective Stille Coupling of Enantiopure Haloallenes and Alkenylstannanes for the Synthesis of Allenyl Carotenoids. Experimental and Computational Studies
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- Gold-Catalyzed Hydrative Carbocyclization of 1,5- and 1,7-Allenynes Mediated by π-Allene Complex: Mechanistic Evidence Supported by the Chirality Transfer of Allenyne Substrates
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- DFT Study on the Diels−Alder Cycloaddition between Alkenyl−M(0) (M = Cr, W) Carbene Complexes and Neutral 1,3-Dienes
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- Allenyl Azide Cycloaddition Chemistry: Exploration of the Scope and Mechanism of Cyclopentennelated Dihydropyrrole Synthesis through Azatrimethylenemethane Intermediates
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- Synthesis and Structural Characterization of Stable Organogold(I) Compounds. Evidence for the Mechanism of Gold-Catalyzed Cyclizations
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- Mechanistic Insights into the Gold-Catalyzed Cycloisomerization of Bromoallenyl Ketones: Ligand-Controlled Regioselectivity
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- Theory of 1,3-Dipolar Cycloadditions: Distortion/Interaction and Frontier Molecular Orbital Models
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- Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles
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- Gold-Catalyzed Cycloisomerization of 1,5-Allenynes via Dual Activation of an Ene Reaction
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- Origins of Differences in Reactivities of Alkenes, Alkynes, and Allenes in [Rh(CO)2Cl]2-Catalyzed (5 + 2) Cycloaddition Reactions with Vinylcyclopropanes
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- Gold-catalyzed intermolecular addition of alcohols toward the allenic bond of 4-vinylidene-2-oxazolidinones
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- Palladium-Catalyzed Selenoacylation of Allenes Leading to the Regioselective Formation of Functionalized Allyl Selenides
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- Regiocontrolled Addition of Arylboronic Acids to Allenes Using Palladium and Platinum Catalysts
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- Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity
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- Regio- and Stereoselective Synthesis of Alkyl Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols
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- Theoretical Studies on the Reaction Mechanism of Platinum-Catalyzed Diboration of Allenes
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- Insertion Reactions of Allenes with Palladium Aryl Complexes [PdI(Ph)(PPh3)]2and PdI(Ph)(dppe)
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- A Mechanism for the Palladium-Catalyzed Regioselective Silaboration of Allene: A Theoretical Study
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- Molecular electrostatic potentials of divalent carbon(0) compounds
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- Recent advances in syntheses of heterocycles and carbocycles via homogeneous gold catalysis. Part 1: Heteroatom addition and hydroarylation reactions of alkynes, allenes, and alkenes
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- Gold(I)-catalyzed hydration of allenes
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- Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight
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- Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination
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- Platinum-Catalyzed Intramolecular [4C+3C] Cycloaddition between Dienes and Allenes
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- Golden Carousel in Catalysis: The Cationic Gold/Propargylic Ester Cycle
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- Alkyne versus Allene Activation in Platinum- and Gold-Catalyzed Cycloisomerization of Hydroxylated 1,5-Allenynes
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- Intramolecular thermal allenyne [2+2] cycloadditions: facile construction of the 5–6–4 ring core of sterpurene
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