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Rapid and Mild Metal-Free Reduction of Epoxides to Primary Alcohols Mediated by HFIP

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

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Aziridines and Epoxides in Organic Synthesis
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Industrial Organic Chemistry
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Generation of a Low‐Valent Titanium Species from Titanatrane and its Catalytic Reactions: Radical Ring Opening of Oxetanes
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Palladium‐Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen
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Supramolecular Catalyst for Aldehyde Hydrogenation and Tandem Hydroformylation–Hydrogenation
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High‐Yielding Tandem Hydroformylation/Hydrogenation of a Terminal Olefin to Produce a Linear Alcohol Using a Rh/Ru Dual Catalyst System
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Tandem Rhodium‐Catalyzed Hydroformylation–Hydrogenation of Alkenes by Employing a Cooperative Ligand System
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Catalytic Hydrogen Atom Transfer (HAT) for Sustainable and Diastereoselective Radical Reduction
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From Olefins to Alcohols: Efficient and Regioselective Ruthenium‐Catalyzed Domino Hydroformylation/Reduction Sequence
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Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis
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Highly Active Titanocene Catalysts for Epoxide Hydrosilylation: Synthesis, Theory, Kinetics, EPR Spectroscopy
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Catalytic Friedel–Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols
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Calcium(II)‐Catalyzed Intermolecular Hydroarylation of Deactivated Styrenes in Hexafluoroisopropanol
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A General Regioselective Synthesis of Alcohols by Cobalt‐Catalyzed Hydrogenation of Epoxides
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Electrochemical 1,2‐Diarylation of Alkenes Enabled by Direct Dual C–H Functionalizations of Electron‐Rich Aromatic Hydrocarbons
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Catalytic Reduction of Cyclic Ethers with Hydrosilanes
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Catalytic Asymmetric Hydroboration: Recent Advances and Applications in Carbon−Carbon Bond‐Forming Reactions
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Reactivity versus Stability of Oxiranes under Palladium‐Catalyzed Reductive Conditions
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Regioselective ring opening of oxetanes by hydrogenolysis. – A convenient method for the carbohydroxylation of enol ethers
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Fluorinated Alcohols: Magic Reaction Medium and Promoters for Organic Synthesis
inferredcites →https://doi.org/10.1016/b978-0-08-052349-1.00079-2openalex-snapshot
Acid-catalyzed Rearrangements of Epoxides
inferredcites →https://doi.org/10.1016/j.chempr.2021.10.023openalex-snapshot
Unlocking the Friedel-Crafts arylation of primary aliphatic alcohols and epoxides driven by hexafluoroisopropanol
inferredcites →https://doi.org/10.1016/j.tet.2008.08.107openalex-snapshot
Titanocene catalyzed opening of oxetanes
inferredcites →https://doi.org/10.1016/s0040-4039(99)01757-8openalex-snapshot
A novel reduction of alcohols and ethers with a HSiEt3catalytic B(C6F5)3 system
inferredcites →https://doi.org/10.1016/s0040-4039(99)01974-7openalex-snapshot
Reductive opening of aziridines with polymethylhydrosiloxane
inferredcites →https://doi.org/10.1016/s0040-4039(99)02147-4openalex-snapshot
Regiospecific reduction of oxetanes with lithium under aprotic conditions
inferredcites →https://doi.org/10.1021/acs.joc.0c00568openalex-snapshot
Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- and α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol
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Hexafluoroisopropanol-Mediated Intramolecular Ring-Opening Cyclization of Indolyl-N-Tethered Epoxides: Tether-Length-Controlled Synthesis of 1,7- and 1,2-Fused Indoles
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Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
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Activation of C–C Bonds via σ-Bond Metathesis: Hydroborenium-Catalyzed Hydrogenolysis of Cyclopropanes
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Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C–C σ-Bonds in Cyclopropanes with iPrOH
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Modular Synthesis of 9,10-Dihydroacridines through an ortho -C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol
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Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
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Tetraphenylphosphonium Tetrafluoroborate/1,1,1,3,3,3-Hexafluoroisopropanol (Ph4PBF4/HFIP) Effecting Epoxide-Initiated Cation–Olefin Polycyclizations
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Hexafluoro-2-propanol-Promoted Intermolecular Friedel–Crafts Acylation Reaction
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Lewis Acid/Hexafluoroisopropanol: A Promoter System for Selective ortho-C-Alkylation of Anilines with Deactivated Styrene Derivatives and Unactivated Alkenes
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Erbium-Catalyzed Regioselective Isomerization–Cobalt-Catalyzed Transfer Hydrogenation Sequence for the Synthesis of Anti-Markovnikov Alcohols from Epoxides under Mild Conditions
inferredcites →https://doi.org/10.1021/acscatal.1c03549openalex-snapshot
Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex
inferredcites →https://doi.org/10.1021/acscatal.6b03388openalex-snapshot
Visible-Light-Mediated Anti-Markovnikov Hydration of Olefins
inferredcites →https://doi.org/10.1021/acscatal.7b00300openalex-snapshot
Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence
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Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol
inferredcites →https://doi.org/10.1021/acscatal.9b01584openalex-snapshot
Cobalt-Catalyzed Hydrogenations via Olefin Cobaltate and Hydride Intermediates
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Transition-metal promoted hydroborations of alkenes, emerging methodology for organic transformations
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Applied Hydroformylation
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The Chemistry of Transition Metals with Three-Membered Ring Heterocycles
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Peracid Reactions. III. 1 The Oxidation of Bicyclo [2.2.1]heptadiene 2
inferredcites →https://doi.org/10.1021/ja067234oopenalex-snapshot
Mild Reductive Opening of Aryl Pyranosides Promoted by Scandium(III) Triflate
inferredcites →https://doi.org/10.1021/ja306309uopenalex-snapshot
Etheric C–O Bond Hydrogenolysis Using a Tandem Lanthanide Triflate/Supported Palladium Nanoparticle Catalyst System
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Tandem Hydroformylation/Hydrogenation of Alkenes to Normal Alcohols Using Rh/Ru Dual Catalyst or Ru Single Component Catalyst
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Sustainable Radical Reduction through Catalytic Hydrogen Atom Transfer
inferredcites →https://doi.org/10.1021/ja9013375openalex-snapshot
Iridium-Catalyzed Asymmetric Hydrogenation Yielding Chiral Diarylmethines with Weakly Coordinating or Noncoordinating Substituents
inferredcites →https://doi.org/10.1021/ja981635popenalex-snapshot
Emergence of a Novel Catalytic Radical Reaction: Titanocene-Catalyzed Reductive Opening of Epoxides
inferredcites →https://doi.org/10.1021/jacs.0c05917openalex-snapshot
Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
inferredcites →https://doi.org/10.1021/jacs.0c13093openalex-snapshot
Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
inferredcites →https://doi.org/10.1021/jacs.1c11791openalex-snapshot
Epoxide Electroreduction
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Metal Nanoparticles Catalyzed Selective Carbon–Carbon Bond Activation in the Liquid Phase
inferredcites →https://doi.org/10.1021/jacs.7b06340openalex-snapshot
Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles
inferredcites →https://doi.org/10.1021/jacs.8b05680openalex-snapshot
Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes
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Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides
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Silane reductions in acidic media. 10. Ionic hydrogenation of cycloalkenes. Stereoselectivity and mechanism
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Carbonium ion-silane hydride transfer reactions. II. 2-Phenyl-2-norbornyl cation
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Recyclable Polyurea-Microencapsulated Pd(0) Nanoparticles: An Efficient Catalyst for Hydrogenolysis of Epoxides
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Iron-Catalyzed Reductive Magnesiation of Oxetanes to Generate (3-Oxidopropyl)magnesium Reagents
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Iterative protecting group-free cross-coupling leading to chiral multiply arylated structures
inferredcites →https://doi.org/10.1038/s41570-017-0088openalex-snapshot
Hexafluoroisopropanol as a highly versatile solvent
inferredcites →https://doi.org/10.1038/s41570-018-0001-2openalex-snapshot
Earth-abundant transition metal catalysts for alkene hydrosilylation and hydroboration
inferredcites →https://doi.org/10.1038/s41586-021-03920-6openalex-snapshot
Metallaphotoredox-enabled deoxygenative arylation of alcohols
inferredcites →https://doi.org/10.1038/s41929-019-0286-7openalex-snapshot
Iron-catalysed regioselective hydrogenation of terminal epoxides to alcohols under mild conditions
inferredcites →https://doi.org/10.1039/b926684dopenalex-snapshot
Friedel–Crafts alkylation of arenes with epoxides promoted by fluorinated alcohols or water
inferredcites →https://doi.org/10.1039/c2cy00450jopenalex-snapshot
“On-water” rhodium-catalysed hydroformylation for the production of linear alcohols
inferredcites →https://doi.org/10.1039/c3ob27285kopenalex-snapshot
Asymmetric rearrangement of racemic epoxides catalyzed by chiral Brønsted acids
inferredcites →https://doi.org/10.1039/c4cc09307kopenalex-snapshot
Photocatalytic hydrogenolysis of epoxides using alcohols as reducing agents on TiO 2 loaded with Pt nanoparticles
inferredcites →https://doi.org/10.1039/c4cy01131gopenalex-snapshot
Production of alcohols via hydroformylation
inferredcites →https://doi.org/10.1039/c7cc01655gopenalex-snapshot
Regioselective hydrosilylation of epoxides catalysed by nickel( ii ) hydrido complexes
inferredcites →https://doi.org/10.1039/c8cc03741hopenalex-snapshot
Piers’ borane-mediated hydrosilylation of epoxides and cyclic ethers
inferredcites →https://doi.org/10.1039/c8cs00883copenalex-snapshot
Emerging unconventional organic solvents for C–H bond and related functionalization reactions
inferredcites →https://doi.org/10.1039/c8re00225hopenalex-snapshot
Role of hexafluoroisopropanol in C–H activation
inferredcites →https://doi.org/10.1039/c9cy00791aopenalex-snapshot
Iridium-promoted conversion of terminal epoxides to primary alcohols under acidic conditions using hydrogen
inferredcites →https://doi.org/10.1039/d0cc05194bopenalex-snapshot
Exploiting hexafluoroisopropanol (HFIP) in Lewis and Brønsted acid-catalyzed reactions
inferredcites →https://doi.org/10.1039/d0sc06937jopenalex-snapshot
Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C–H activation
inferredcites →https://doi.org/10.1126/science.1208685openalex-snapshot
Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis
inferredcites →https://doi.org/10.1126/science.233.4768.1069openalex-snapshot
Catalytic Hydration of Terminal Alkenes to Primary Alcohols
inferredcites →https://doi.org/10.1126/science.aao1482openalex-snapshot
Anti-Markovnikov alkene oxidation by metal-oxo–mediated enzyme catalysis
inferredcites →https://doi.org/10.1126/science.aaw3913openalex-snapshot
Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis
inferredcites →https://doi.org/10.2174/1385272053765060openalex-snapshot
Recent Advances in Organic Synthesis Using Transition Metal-Catalyzed Hydroborations

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Design of New Efficient Carborane Molecular Scaffolds Utilizing Functionalization of C=C Double Bonds in Boron‐Substituted Allylcarboranes
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Synthesis of Unprotected β‐Arylethylamines by Iron(II)‐Catalyzed 1,2‐Aminoarylation of Alkenes in Hexafluoroisopropanol
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Coupling Titanium and Chromium Catalysis in a Reaction Network for the Reprogramming of [BH4]− as Electron Transfer and Hydrogen Atom Transfer Reagent for Radical Chemistry
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Synthesis of Unprotected β‐Arylethylamines by Iron(II)‐Catalyzed 1,2‐Aminoarylation of Alkenes in Hexafluoroisopropanol
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Coupling Titanium and Chromium Catalysis in a Reaction Network for the Reprogramming of [BH 4 ] − as Electron Transfer and Hydrogen Atom Transfer Reagent for Radical Chemistry
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Polymethylhydrosiloxane (PMHS) as Sustainable Reductant in the Titanocene Catalyzed Epoxide Hydrosilylation
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Ab Initio Metadynamics Simulations of Hexafluoroisopropanol Solvent Effects: Synergistic Role of Solvent H‐Bonding Networks and Solvent‐Solute C−H/π Interactions
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Highly Efficient Organocatalytic House‐Meinwald Rearrangement for the Facile Synthesis of Aldehydes: Swift Access to Ibuprofen
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A General Strategy for the Synthesis of Jerangolids Enabled by π‐allyl Stille Coupling
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Total Syntheses of Favolasins A, E, G and K, Polyketides Isolated from Cultures of the Basidiomycetes Fungi Favolaschia sp. BCC 18686 and Favolaschia calocera BCC 36684
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Hexafluoroisopropanol Promoted Ring‐Opening‐Cyclization of Donor–Acceptor Cyclopropanes with Primary Amines
inferred← citeshttps://doi.org/10.1002/ejoc.202400533openalex-snapshot
HFIP‐Promoted Short Total Synthesis of Gochnatiolide D and Ainsliadimer A from Dehydrozaluzanin C
inferred← citeshttps://doi.org/10.1002/gch2.202200240openalex-snapshot
Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions
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Hydrogenation of Epoxides to Anti‐Markovnikov Alcohols over a Nickel Heterogenous Catalyst Prepared from Biomass (Rice) Waste
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Acid-Catalyzed Rearrangement of Epoxides
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Reduction of Epoxides
inferred← citeshttps://doi.org/10.1016/b978-0-443-21936-8.00003-3openalex-snapshot
Three-membered ring systems
inferred← citeshttps://doi.org/10.1016/j.tet.2024.133943openalex-snapshot
HFIP-promoted synthesis of imidazo [1,2-a]pyridines containing CF3-substituted tertiary alcohols at room temperature
inferred← citeshttps://doi.org/10.1016/j.tetlet.2023.154716openalex-snapshot
House-Meinwald rearrangement of aryl-substituted epoxysulfones in hexafluoroisopropanol (HFIP)
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Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF3-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles
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Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2–N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl(2-benzothienyl)methanols
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Difunctionalization Processes Enabled by Hexafluoroisopropanol
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Formal anti-Markovnikov hydration of alkenes via paired electrolysis intercepting water-splitting
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Proline-catalyzed synthesis of α-substituted ( E )-α,β-unsaturated aldehydes from epoxides
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Transition-metal-free chemoselective reduction of α,β-unsaturated ketones using H 2 O as a hydrogen source
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Metal-free electrochemical anti-markovnikov hydration of aryl alkenes
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Organocatalytic, Chemoselective, and Stereospecific House–Meinwald Rearrangement of Trisubstituted Epoxides
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Tandem Cooperative Friedel-Crafts Reaction of Aldehydes with Electron Deficient Arenes Through Catalyst-Activation via Hydrogen Bonding Network
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Tandem Cooperative Friedel-Crafts Reaction of Aldehydes with Electron Deficient Arenes Through Catalyst-Activation via Hydrogen Bonding Network
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Nickel-Catalyzed Reductive Cyanation of Aryl Halides and Epoxides with Cyanogen Bromide
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