Nickel-Catalyzed Carboxylation of Aryl and Heteroaryl Fluorosulfates Using Carbon Dioxide.

The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.

• Publication year

  2019

• Venue

  Organic Letters

• Publication date

  2019-03-26

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.9b00836PMID 30912447
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• transesterification

  2020cited by this paper
• Synthesis and Chemical Transformations of Fluorosulfates

  2018cited by this paper
• Transition metal-catalyzed carboxylation of unsaturated substrates with CO2

  2018cited by this paper
• Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2.

  2018cited by this paper
• Rhodium(II)-Catalyzed Aryl C−H Carboxylation of 2-Pyridylphenols with CO2

  2018cited by this paper
• A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an "F-SO2 +" Donor of Unprecedented Reactivity, Selectivity, and Scope.

  2018cited by this paper
• Reactions of Arylsulfonate Electrophiles with NMe4F: Mechanistic Insight, Reactivity, and Scope.

  2018cited by this paper
• Ligand-enabled site-selectivity in a versatile rhodium(ii)-catalysed aryl C–H carboxylation with CO2

  2018cited by this paper
• Catalytic Lactonization of Unactivated Aryl C-H Bonds with CO2: Experimental and Computational Investigation.

  2018cited by this paper
• Transition-Metal-Catalyzed Carboxylation Reactions with Carbon Dioxide.

  2018cited by this paper
• Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO2 to Generate α,α-Disubstituted α-Amino Acids.

  2018cited by this paper
• Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts.

  2018cited by this paper
• Photochemical Carboxylation of Activated C(sp3 )-H Bonds with CO2.

  2017cited by this paper
• Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water.

  2017cited by this paper
• Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts.

  2017cited by this paper
• Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates.

  2017cited by this paper
• Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide.

  2017cited by this paper
• Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates.

  2017cited by this paper
• Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light-Nickel Catalysis.

  2017cited by this paper
• Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide

  2017cited by this paper
• Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide

  2017cited by this paper
• SO2 F2 -Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide.

  2017cited by this paper
• Metal-Catalyzed Carboxylation of Organic (Pseudo)halides with CO2

  2016cited by this paper
• Capture of CO2 by a Cationic Nickel(I) Complex in the Gas Phase and Characterization of the Bound, Activated CO2 Molecule by Cryogenic Ion Vibrational Predissociation Spectroscopy.

  2016cited by this paper
• Direct Carboxylation of Aryl Tosylates by CO2 Catalyzed by In situ-Generated Ni(0).

  2016cited by this paper
• Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

  2016cited by this paper
• Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates.

  2015cited by this paper
• Using carbon dioxide as a building block in organic synthesis

  2015cited by this paper
• Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO2.

  2015cited by this paper
• Nickel- and Palladium-Catalyzed Coupling of Aryl Fluorosulfonates with Aryl Boronic Acids Enabled by Sulfuryl Fluoride

  2015cited by this paper
• SuFEx-based synthesis of polysulfates.

  2014cited by this paper
• Ni-catalyzed carboxylation of C(sp2)- and C(sp3)-O bonds with CO2.

  2014cited by this paper
• Chemicals from coal coking.

  2014cited by this paper
• Direct carboxylation of simple arenes with CO₂ through a rhodium-catalyzed C-H bond activation.

  2014cited by this paper
• Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.

  2014cited by this paper
• Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

  2013cited by this paper
• Ni-catalyzed direct carboxylation of benzyl halides with CO2.

  2013cited by this paper
• The crucial role of a Ni(I) intermediate in Ni-catalyzed carboxylation of aryl chloride with CO2: a theoretical study.

  2013cited by this paper
• Direct C-H carboxylation with carbon dioxide using 1,2,3-triazol-5-ylidene copper(I) complexes.

  2012cited by this paper
• Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide.

  2012cited by this paper
• Carbon dioxide as a carbon source in organic transformation: carbon-carbon bond forming reactions by transition-metal catalysts.

  2012cited by this paper
• Rhodium(I)-catalyzed direct carboxylation of arenes with CO2 via chelation-assisted C-H bond activation.

  2011cited by this paper
• Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide.

  2011cited by this paper
• Transition-metal-catalyzed carboxylation of C-H bonds.

  2011cited by this paper
• Myth or reality? Fixation of carbon dioxide into complex organic matter under mild conditions.

  2011cited by this paper
• Carboxylation of N-H/C-H bonds using N-heterocyclic carbene copper(I) complexes.

  2010cited by this paper
• Phenolic Resins: A Century of Progress

  2010cited by this paper
• Carboxylation of C-H bonds using N-heterocyclic carbene gold(I) complexes.

  2010cited by this paper
• Carbon dioxide as chemical feedstock

  2010cited by this paper
• Copper-catalyzed direct carboxylation of C-H bonds with carbon dioxide.

  2010cited by this paper
• Metal-catalyzed carboxylation of organometallic reagents with carbon dioxide.

  2009cited by this paper
• Palladium-catalyzed direct carboxylation of aryl bromides with carbon dioxide.

  2009cited by this paper
• Transformation of carbon dioxide.

  2007cited by this paper
• Carboxylation and esterification of functionalized arylcopper reagents.

  2005cited by this paper
• The chemistry of phenols

  2003cited by this paper
• A Novel, Practical Synthesis of Estra-1,3,5(10)-triene-3,17.beta.-dicarboxylic Acid 17-tert-Butylamide (SK&F 105656) from Estrone, via a Palladium-Catalyzed Methoxycarbonylation of a 3-Fluorosulfonate

  1994cited by this paper
• Nickel-Complex-Promoted Carboxylation of Haloarenes Involving Insertion of CO2 into NiII-C Bonds

  1994cited by this paper
• Palladium cross-coupling reactions of aryl fluorosulfonates: an alternative to triflate chemistry

  1991cited by this paper
• A survey of Hammett substituent constants and resonance and field parameters

  1991cited by this paper
• Synthesis of Carboxylic Acids, Esters and Their Derivatives

  1991cited by this paper
• Reactions of carbon dioxide with carbon-carbon bond formation catalyzed by transition-metal complexes

  1988cited by this paper
• The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives

  1937cited by this paper

• Iron-Catalyzed Reductive Carboxylation of Arenes with CO2 via Thianthrenium Salts.

  2025cites this paper
• Ni- and Cu-Promoted Fixation Reactions of Carbon Dioxide with Unsaturated Hydrocarbons

  2025cites this paper
• Synthesis of Polyfluorinated Biaryls via Palladium-Catalyzed Decarboxylative Cross-Coupling of Zinc Polyfluorobenzoates with Aryl Fluorosulfates.

  2025cites this paper
• CO2 Fixation into Useful Aromatic Carboxylic Acids via C (sp2)–X Bonds Functionalization

  2025cites this paper
• Palladium-catalyzed α-arylation of sulfoxonium ylides with aryl fluorosulfates.

  2025cites this paper
• Iron-Catalyzed Carboxylation of Pyridylphosphonium Salts with CO2.

  2025cites this paper
• Palladium-Catalyzed α-Arylation of Nitroalkanes with Aryl Fluorosulfonates for Convenient Access to α-Arylated Nitroalkanes.

  2025cites this paper
• Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates

  2024cites this paper
• Isolation and Reactivity of Arylnickel(II) Complexes in Nickel-Catalyzed Borylation of Aryl Fluorosulfates

  2024cites this paper
• Visible-light-driven synthesis of N-heteroaromatic carboxylic acids by thiolate-catalysed carboxylation of C(sp²)–H bonds using CO2

  2024cites this paper
• Efficient palladium-catalyzed electrocarboxylation enables late-stage carbon isotope labelling

  2024cites this paper
• Organocatalytic SuFEx click reactions of SO2F2.

  2024cites this paper
• Reversal of Reactivity of Heyns Intermediate for the Concise Synthesis of Substituted 3-Hydroxyquinolines.

  2024cites this paper
• Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C-O Bond Cleavage.

  2024cites this paper
• Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate

  2024cites this paper
• Rapid  aminations of functionalized aryl fluorosulfates in water.

  2024cites this paper
• Nickel-catalyzed cross-electrophile couplings of aryl fluorosulfates with vinyl chlorosilanes

  2024cites this paper
• Nickel-Catalyzed Direct Cross-Coupling of Aryl Fluorosulfates with Aryl Bromides.

  2023cites this paper
• Recent progress in reductive carboxylation of C–O bonds with CO2

  2023cites this paper
• New Chemical Transformations Involving SO2F2‐Mediated Alcohol Activation

  2023cites this paper
• Ruthenium-catalyzed Synthesis of Aryl and Alkenyl Halides from Fluorosulfonates.

  2023cites this paper
• Aryl fluorosulfates: powerful and versatile partners in cross-coupling reactions

  2023cites this paper
• Regioselective umpolung para-C–H functionalization of arylhydroxylamines

  2023cites this paper
• Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust

  2023cites this paper
• Direct 18F-Fluorosulfurylation of Phenols and Amines Using an [18F]FSO2+ Transfer Agent Generated In Situ.

  2023cites this paper
• External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

  2023cites this paper
• Pd(II)-catalyzed carboxylation of aromatic C─H bonds with CO2

  2023cites this paper
• Challenges and recent advancements in the transformation of CO2 into carboxylic acids: straightforward assembly with homogeneous 3d metals.

  2022cites this paper
• Suzuki-Miyaura Cross-Coupling of Aryl Fluorosulfonates Mediated by Air- and Moisture-stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Broad Platform for C-O Cross-Coupling of Stable Phenolic Electrophiles.

  2022cites this paper
• Visible-Light Photoredox-Catalyzed Carboxylation of Activated C(sp3)─O Bonds with CO2

  2021cites this paper
• Synthesis and characterization of nickel immobilized on aminated Periodic Mesoporous Organosilica

  2021cites this paper
• Ligand-Controlled Regiodivergent Catalytic Amidation of Unactivated Secondary Alkyl Bromides

  2021cites this paper
• Deoxyfluorination of alcohols with aryl fluorosulfonates.

  2021cites this paper
• Mechanistic Studies into Visible Light-Driven Carboxylation of Aryl Halides/Triflates by the Combined Use of Palladium and Photoredox Catalysts

  2021cites this paper
• Nickel‐ and Palladium‐Catalyzed Cross‐Coupling of Aryl Fluorosulfonates and Phosphites: Synthesis of Aryl Phosphonates

  2021cites this paper
• Direct Carboxylation with Carbon Dioxide via Cooperative Photoredox and Transition‐Metal Dual Catalysis

  2021cites this paper
• Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride.

  2021cites this paper
• Enantioselective CO2 Fixation Via a Heck-Coupling/Carboxylation Cascade Catalyzed by Nickel.

  2021cites this paper
• Applications of Nickel(II) compounds in Organic Synthesis.

  2021cites this paper
• Visible-light photoredox-catalyzed carboxylation of benzyl halides with CO2: Mild and transition-metal-free

  2021cites this paper
• Copper(I)-Mediated 11C-Carboxylation of (Hetero)arylstannanes

  2020cites this paper
• Reversible Insertion of Carbon Dioxide at Phosphine Sulfonamido PdII–Aryl Complexes

  2020cites this paper
• SO2F2-mediated deoxygenative C2-sulfonylation of quinoline N-oxides with sodium sulfinates

  2020cites this paper
• Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide

  2020cites this paper
• Theoretical research on the direct carboxylation of benzene with CO 2 catalyzed by different carbene‐CuOH compounds

  2020cites this paper
• Ni-Catalyzed Carboxylation of C(sp2)–S Bonds with CO2: Evidence for the Multifaceted Role of Zn

  2020cites this paper
• Palladium-Catalyzed Cross-Couplings by C-O Bond Activation.

  2020cites this paper
• Halide-Accelerated Acyl Fluoride Formation Using Sulfuryl Fluoride.

  2020cites this paper
• Properties and Applications of Sulfur(VI) Fluorides

  2020cites this paper
• Catalytic Decarboxylation/Carboxylation Platform for Accessing Isotopically Labeled Carboxylic Acids

  2019cites this paper
• Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of para-amino-arylfluorosulfates.

  2019cites this paper
• Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts.

  2019cites this paper
• Chemoselektive, modulare Diversifikation polyhalogenierter Arylfluorosulfate (ArOSO 2 F), ermöglicht durch ein luftstabiles Pd I ‐Dimer

  2019cites this paper
• Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts.

  2019cites this paper
• Site‐Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2F) Enabled by an Air‐Stable PdI Dimer

  2019cites this paper
• Introduction of Aryl Fluorosulfates into the Realm of Catellani Reaction Substrates.

  2019cites this paper
• Applications of sulfuryl fluoride (SO2F2) in chemical transformations

  2019cites this paper
• Photo-assisted Fixation of CO2 onto Aryl Bromides Producing Aromatic Esters

  2019cites this paper
• Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr 4 /MeOH

  2019cites this paper
• E�cient palladium-catalyzed electrocarboxylation enables late-stage carbon isotope labelling

  year unknowncites this paper