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Synthesis of Difluoromethylated Carbinols via a HFIP-Promoted Hydroxydifluoromethylation of Aniline, Indole, and Pyrrole Derivatives with Difluoroacetaldehyde Ethyl Hemiacetal

https://doi.org/10.1021/acs.joc.2c02812

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What this work says

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

inferredcites →https://doi.org/10.1002/ajoc.201700320openalex-snapshot

Hexafluoroisopropanol‐Promoted Metal‐Free Allylation of Silyl Enol Ethers with Allylic Alcohols

inferredcites →https://doi.org/10.1002/anie.201605280openalex-snapshot

Bis(difluoromethyl)trimethylsilicate Anion: A Key Intermediate in Nucleophilic Difluoromethylation of Enolizable Ketones with Me3SiCF2H

inferredcites →https://doi.org/10.1002/anie.201814607openalex-snapshot

Direct Catalytic Asymmetric Aldol Reaction of α‐Alkoxyamides to α‐Fluorinated Ketones

inferredcites →https://doi.org/10.1002/ejoc.201000712openalex-snapshot

Enantiomerically Pure and Highly Substituted Alicyclic α,α‐Difluoro Ketones: Potential Inhibitors for Malarial Aspartic Proteases, the Plasmepsins

inferredcites →https://doi.org/10.1016/j.cclet.2020.03.050openalex-snapshot

Fluorine-containing drugs approved by the FDA in 2019

inferredcites →https://doi.org/10.1016/j.cclet.2021.07.064openalex-snapshot

Fluorine-containing agrochemicals in the last decade and approaches for fluorine incorporation

inferredcites →https://doi.org/10.1016/j.cclet.2021.12.002openalex-snapshot

HFIP-catalyzed highly diastereoselective formal [4 + 2] cyclization to synthesize difluorinated multisubstituted chromans using difluoroenoxysilanes as C2 synthons

inferredcites →https://doi.org/10.1016/j.jfluchem.2013.02.023openalex-snapshot

On the polarity of partially fluorinated methyl groups

inferredcites →https://doi.org/10.1016/j.tetlet.2018.07.021openalex-snapshot

Decarboxylative difluoromethylation of aldehydes with PhSO 2 CF 2 COOK: A facile and efficient access to difluoromethylated carbinols

inferredcites →https://doi.org/10.1021/acs.chemrev.1c00749openalex-snapshot

HFIP in Organic Synthesis

inferredcites →https://doi.org/10.1021/acs.chemrev.5b00392openalex-snapshot

Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

inferredcites →https://doi.org/10.1021/acs.jmedchem.5b00258openalex-snapshot

Applications of Fluorine in Medicinal Chemistry

inferredcites →https://doi.org/10.1021/acs.jmedchem.6b01691openalex-snapshot

Difluoromethyl Bioisostere: Examining the “Lipophilic Hydrogen Bond Donor” Concept

inferredcites →https://doi.org/10.1021/acs.jmedchem.9b00604openalex-snapshot

CF 2 H, a Functional Group-Dependent Hydrogen-Bond Donor: Is It a More or Less Lipophilic Bioisostere of OH, SH, and CH 3 ?

inferredcites →https://doi.org/10.1021/acs.jmedchem.9b01877openalex-snapshot

Metabolic and Pharmaceutical Aspects of Fluorinated Compounds

inferredcites →https://doi.org/10.1021/acs.joc.0c01207openalex-snapshot

HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling

inferredcites →https://doi.org/10.1021/acs.joc.1c02504openalex-snapshot

Synthesis of 2,2-Difluoro-3-hydroxy-1,4-diketones via an HFIP-Catalyzed Mukaiyama Aldol Reaction of Glyoxal Monohydrates with Difluoroenoxysilanes

inferredcites →https://doi.org/10.1021/acs.joc.1c03155openalex-snapshot

HFIP-Promoted Selective Hydroxyalkylation of Aniline Derivatives with Arylglyoxal Hydrates

inferredcites →https://doi.org/10.1021/acs.orglett.1c00031openalex-snapshot

TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2- a ]pyridines with Fluorinated Alcohols

inferredcites →https://doi.org/10.1021/acs.orglett.1c02659openalex-snapshot

HFIP-Catalyzed Difluoroalkylation of Propargylic Alcohols to Access Tetrasubstituted Difluoroalkyl Allenes

inferredcites →https://doi.org/10.1021/cr100166aopenalex-snapshot

Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates

inferredcites →https://doi.org/10.1021/cr4002879openalex-snapshot

Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)

inferredcites →https://doi.org/10.1021/cr500277bopenalex-snapshot

Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions

inferredcites →https://doi.org/10.1021/jacs.7b04457openalex-snapshot

CF 2 H, a Hydrogen Bond Donor

inferredcites →https://doi.org/10.1021/jo400202wopenalex-snapshot

Nucleophilic Trifluoromethylation of Carbonyl Compounds: Trifluoroacetaldehyde Hydrate as a Trifluoromethyl Source

inferredcites →https://doi.org/10.1021/jo400962copenalex-snapshot

Synthesis of Enantiopure Fluorohydrins Using Alcohol Dehydrogenases at High Substrate Concentrations

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/d0cc06980aopenalex-snapshot

HFIP-catalyzed direct dehydroxydifluoroalkylation of benzylic and allylic alcohols with difluoroenoxysilanes

inferredcites →https://doi.org/10.1039/d1sc01574eopenalex-snapshot

Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions

inferredcites →https://doi.org/10.1039/d2qo01277dopenalex-snapshot

Synthesis of difluoromethyl carbinols from the Friedel–Crafts reaction of electron-rich arenes with difluorovinyl arylsulfonates

inferredcites →https://doi.org/10.1055/s-0029-1218712openalex-snapshot

Noncatalytic Electrophilic Oxyalkylation of Anilines with 2-Trifluoroacetyl-1,3-benzothiazole

inferredcites →https://doi.org/10.1111/jphp.12507openalex-snapshot

Antioxidant properties in a non-polar environment of difluoromethyl bioisosteres of methyl hydroxycinnamates

What points at this work

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

inferred← citeshttps://doi.org/10.2139/ssrn.4682376openalex-extracted

inferred← citeshttps://doi.org/10.1002/adsc.70304openalex-snapshot

Hexafluoroisopropanol‐Enabled One‐Step Access to Oxetanol and Azetidinol Scaffolds from Unprotected Indoles and Heteroarenes

inferred← citeshttps://doi.org/10.1002/ajoc.70360openalex-snapshot

Fluoroalkyl Acetaldehydes‐Versatile Fluorinated Building Blocks for the Synthesis of Diverse Fluoroalkylated Compounds

inferred← citeshttps://doi.org/10.1016/b978-0-443-33494-8.00005-6openalex-snapshot

Five-membered ring systems: Pyrroles and benzo analogs

inferred← citeshttps://doi.org/10.1016/j.jscs.2024.101883openalex-snapshot

Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives

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.tet.2025.134844openalex-snapshot

HFIP-triggered C3-hydroalkylation of imidazo[1,2-a]pyridines with maleimides

inferred← citeshttps://doi.org/10.1021/acs.joc.3c01366openalex-snapshot

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) Promoted N-Alkylation of Quinazolinones through Nucleophilic Substitution of Benzyl Alcohols

inferred← citeshttps://doi.org/10.1021/acs.joc.3c02457openalex-snapshot

Regio- and Stereoselective Hexafluoroisopropoxylation and Trifluoroethoxylation of Allenamides

inferred← citeshttps://doi.org/10.1021/acs.joc.4c01208openalex-snapshot

Hexafluoroisopropanol (HFIP)-Mediated Intramolecular Cyclization of Allenamides To Access C1-Vinyl Tetrahydro-β-carbolines

inferred← citeshttps://doi.org/10.1021/acs.joc.4c02330openalex-snapshot

Silver-Catalyzed Cascade Radical Isonitrile Insertion/Defluorinative Cyclization: Direct Synthesis of 4-CF2H-2-Phosphinoyl-quinolines

inferred← citeshttps://doi.org/10.1021/acs.joc.5c00326openalex-snapshot

HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature

inferred← citeshttps://doi.org/10.1021/acs.joc.6c00597openalex-snapshot

HFIP-Promoted Regioselective Allylation of Tetrahydroquinolines (C6) and Indolines (C5) with Vinyl Benzoxazinanones

inferred← citeshttps://doi.org/10.1021/acs.orglett.5c04058openalex-snapshot

Ag 2 O/TBAI Initiated Nucleophilic Difluoromethylation of Carbonyl Compounds with Me 3 SiCF 2 H

inferred← citeshttps://doi.org/10.1039/d3ob01570jopenalex-snapshot

Transition-metal-free and additive-free intermolecular hydroarylation of alkenes with indoles in hexafluoroisopropanol

inferred← citeshttps://doi.org/10.1039/d3ob01582copenalex-snapshot

Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o -hydroxyaryl enaminones

inferred← citeshttps://doi.org/10.1039/d3ob01735dopenalex-snapshot

Divergent synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines

inferred← citeshttps://doi.org/10.1039/d3qo01606dopenalex-snapshot

Visible-light-promoted desulfonylative radical difluoroalkylation between difluoroenol silyl ethers and difluoroalkyl sulfones to construct functionalized aryltetrafluoroethane derivatives

inferred← citeshttps://doi.org/10.1039/d4gc03917copenalex-snapshot

Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP–B(C 6 F 5 ) 3 adduct

inferred← citeshttps://doi.org/10.1039/d4ob01158aopenalex-snapshot

One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon

inferred← citeshttps://doi.org/10.1039/d5cc00154dopenalex-snapshot

HFIP-mediated cascade aminomethylation and intramolecular cyclization of allenamides with N , O -acetals to access tetrahydro-β-carboline derivatives

inferred← citeshttps://doi.org/10.1039/d5gc00878fopenalex-snapshot

Facile and rapid access to hexafluoroisopropanol (HFIP)-group-functionalized aniline and indole derivatives using hexafluoroacetone trihydrate in HFIP

inferred← citeshttps://doi.org/10.1055/a-2254-0907openalex-snapshot

Metal-Free Synthesis of Trifluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines via Dehydrative Coupling of Imidazo[1,2-a]pyridines with Trifluoroacetaldehyde

inferred← citeshttps://doi.org/10.3390/molecules28227522openalex-snapshot

1,1,1,3,3,3-Hexafluoro-2-Propanol-Promoted Friedel–Crafts Reaction: Metal-Free Synthesis of C3-Difluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines at Room Temperature

inferred← citeshttps://doi.org/10.6023/a25070255openalex-snapshot

Three-Component Tandem Cyclization for the Synthesis of Chromone Derivatives from ortho-Hydroxyaryl Enaminones

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