☆ 4.5 Review

Recent Advances in C-F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines

SYNTHESIS-STUTTGART (2022)

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Article Chemistry, Organic

Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction

Qiang Chen et al.

Summary: This Letter describes a palladium/copper-cocatalyzed arylsilylation of internal alkynes with acyl fluorides and silylboranes, resulting in tetrasubstituted alkenylsilanes in moderate to good yields. It is the first example of utilizing acyl fluorides for a three-component coupling reaction via decarbonylation.

ORGANIC LETTERS (2022)

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Review Chemistry, Organic

Photochemical and electrochemical strategies in C-F bond activation and functionalization

Zhanghong Wang et al.

Summary: In summary, the activation and functionalization of C-F bonds are important tools for organic synthesis. Recent developments using photochemical or electrochemical methods have shown significant progress in this field, providing alternative approaches to traditional chemical methods.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Multidisciplinary

Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans

Xiaoye Yu et al.

Summary: In this study, a method using aroyl fluorides as bifunctional reagents for the dearomatization of dihydrobenzofurans was reported. The reaction proceeds through cooperative NHC/photoredox catalysis, resulting in the formation of 2,3-difunctionalized dihydrobenzofuran compounds with moderate to high yield and high diastereoselectivity. The reaction also exhibits broad substrate scope and high functional group compatibility.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Review Chemistry, Multidisciplinary

Selective Decarbonylation via Transition-Metal-Catalyzed Carbon- Carbon Bond Cleavage

Hong Lu et al.

Summary: Transition-metal-catalyzed decarbonylation via carbon-carbon bond cleavage is a crucial synthetic methodology. This method offers a distinct synthetic strategy using carbonyl groups as traceless handles. Significant progress has been made in recent years in various aspects of this reaction.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Zhijun Zuo et al.

Summary: This study presents a cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis. The key step involves a radical/radical cross coupling, leading to metal-free reaction conditions and a wide range of functional group tolerances.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed Decarbonylative Cyanation of Acyl Fluorides and Chlorides

Shun Sakurai et al.

Summary: The decarbonylative cyanation of acyl fluorides can be catalyzed by a Pd/Xantphos system, which is also applicable to the conversion of acyl chlorides.

CHEMISTRY LETTERS (2021)

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Article Chemistry, Multidisciplinary

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

Hayato Fujimoto et al.

Summary: The phosphine-catalyzed hydrovinylation reaction involves a three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The success of the reaction is attributed to the formal transmetalation between pentacoordinate P(V) species and a silyl enol ether, enabling C-C bond formation between polarity-mismatched sites. This bond formation, not achievable by transition metal catalysis, is achieved through a P(III)/P(V) manifold.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis

Naish Lalloo et al.

Summary: This article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction. By optimizing the individual steps of the catalytic cycle to identify compatible coupling partners and an appropriate Pd catalyst, an efficient method for decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride was achieved.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

Kun Liu et al.

Summary: N-Heterocyclic carbene (NHC) catalysis is a versatile tool in modern synthetic chemistry, often used in concert with a second catalytic moiety to expand reaction scope. Triple catalysis, merging three different catalytic modes in a single process, has been recently studied, allowing for the synthesis of complex compounds. In a reported study, alpha-C-H acylation of alkenes using NHC, sulfinate, and photoredox cooperative triple catalysis was achieved, highlighting the potential of such synergistic catalytic systems.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids

Bangyue He et al.

Summary: This Rh-catalyzed decarbonylative C-H coupling method allows alkyl, aryl, and alkenyl carboxylic acids to undergo coupling with amide substrates bearing ortho-Csp(2)-H bonds, leading to generally good yields. It also enables the functionalization of structurally complex carboxyl-containing natural products and pharmaceuticals as well as pharmaceutical amide derivatives by in situ conversion of carboxylic acids into acid fluorides.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

C-H Bond Functionalization Using Pd- and Au-Supported Catalysts with Mechanistic Insights of the Active Species

Tamao Ishida et al.

Summary: The review provides an overview of C-H functionalization reactions, with a focus on reactions involving Pd- and Au-supported catalysts. Key topics covered include reaction mechanisms, active species, leaching, and reusability.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Organic

Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation

Jingwen You et al.

Summary: A nickel-catalyzed decarbonylative thioetherification of acyl fluorides has been developed, allowing a wide range of functional groups to react with thiophenols and obtain corresponding sulfides in good to excellent yields. This protocol provides a highly efficient way to form diverse carbon-sulfur bonds.

SYNTHESIS-STUTTGART (2021)

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Article Multidisciplinary Sciences

Benzylic C-H acylation by cooperative NHC and photoredox catalysis

Qing-Yuan Meng et al.

Summary: Methods enabling site-selective acylation of sp3 C-H bonds in complex organic molecules are not well explored. Here, the authors present a direct and site-selective acylation of benzylic C-H bonds through the combination of N-heterocyclic carbene (NHC) and photoredox catalysis, offering options for preparing benzyl aryl ketones.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

YCatalyzed Intramolecular Aromatic C-H Acylation of 2-Arylbenzoyl Fluorides

Yuka Sakurai et al.

Summary: The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)(2)/PCy3 system is described, which can be applied to the synthesis of indenofluorenedione derivatives and the construction of other molecules with fivemembered rings. The reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds, using a wide range of 2-arylbenzoyl fluoride derivatives as fluorenone precursors.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2021)

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Review Chemistry, Multidisciplinary

Acyclic Twisted Amides

Guangrong Meng et al.

Summary: This contribution provides a comprehensive overview of acyclic twisted amides since 1993, focusing on their key structural properties and applications in various fields of chemistry.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Synthesis of N-CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3 Carbamoyl Fluorides

Christian D. -T. Nielsen et al.

Summary: The study reported a synthetic method for N-trifluoromethyl alkynamides and found that this synthetic compound can serve as a platform to unlock access to other valuable derivatives.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

William D. G. Brittain et al.

Summary: This work utilizes pentafluoropyridine (PFP) in the deoxyfluorination of carboxylic acids to acyl fluorides and in a one-pot amide bond formation. The method allows for high yields of amides to be readily obtained under mild conditions.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI2 and D2O

Hengzhao Li et al.

Summary: A highly chemoselective reductive deuteration of acyl fluorides using SmI2 and D2O as the deuterium source has been developed, providing alpha,alpha-dideuterio alcohols with exceptional levels of deuterium incorporation. This method introduces acyl fluorides as attractive radical precursors for the generation of reactive acyl-type fluoride ketyls, which should have widespread application in synthetic strategies involving single electron transfer processes.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions

Qiang Chen et al.

Summary: A nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes under copper-free conditions was described. This newly developed method has a wide substrate scope, providing internal silylethynes in moderate to high yields. The formation of 1,3-diynes as homocoupled products and conjugate enones as carbonyl-retentive products were effectively suppressed in this reaction.

SYNLETT (2021)

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Review Chemistry, Multidisciplinary

Acyl Fluorides in Late-Transition-Metal Catalysis

Yohei Ogiwara et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Applied

Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides

Muzaffar Kayumov et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Organic

Palladium-Catalyzed Decarbonylative Alkylation of Acyl Fluorides

Liyan Fu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Inorganic & Nuclear

Benzoyl Fluorides as Fluorination Reagents: Reconstruction of Acyl Fluorides via Reversible Acyl C-F Bond Cleavage/Formation in Palladium Catalysis

Yohei Ogiwara et al.

ORGANOMETALLICS (2020)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids

Jiang Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions

Xiu Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Cooperative NHC and Photoredox Catalysis for the Synthesis of β-Trifluoromethylated Alkyl Aryl Ketones

Qing-Yuan Meng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates

Liyan Fu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate

Hayato Fujimoto et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Physical

Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Jing Cao et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah's reagent under solvent-free conditions

Yumeng Liang et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Carbamoyl Fluoride-Enabled Enantioselective Ni-Catalyzed Carbocarbamoylation of Unactivated Alkenes

Yue Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Efficient cleavage of tertiary amide bonds via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system

Zhe Wang et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Multidisciplinary

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: synthesis of unsymmetrical diarylethynes

Qiang Chen et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Iridium-catalyzed Decarbonylative Coupling of Acyl Fluorides with Arenes and Heteroarenes via C-H Activation

Shun Sakurai et al.

CHEMISTRY LETTERS (2019)

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Article Chemistry, Multidisciplinary

Catalytic C-H/C-F Coupling of Azoles and Acyl Fluorides

Yohei Ogiwara et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

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Article Chemistry, Multidisciplinary

Nickel-Copper-Catalyzed Hydroacylation of Vinylarenes with Acyl Fluorides and Hydrosilanes

Yusuke Ueda et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

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Article Biochemistry & Molecular Biology

Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions

Xiu Wang et al.

MOLECULES (2019)

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Article Chemistry, Organic

Enones from Acid Fluorides and Vinyl Triflates by Reductive Nickel Catalysis

Feng-Feng Pan et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Physical

PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp3)-O Bond Cleavage Accelerated by TBAT

Zhenhua Wang et al.

CATALYSTS (2019)

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Article Chemistry, Multidisciplinary

Nickel/copper-cocatalyzed decarbonylative silylation of acyl fluorides

Xiu Wang et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides

Sinead T. Keaveney et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium

Rachel M. Gillard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Organic

Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Yohei Ogiwara et al.

ORGANIC LETTERS (2018)

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Article Multidisciplinary Sciences

Base-free nickel-catalysed decarbonylative Suzuki-Miyaura coupling of acid fluorides

Christian A. Malapit et al.

NATURE (2018)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Fluorides Assisted by Lewis-Acidic Organoboranes

Yasuhiro Okuda et al.

ACS OMEGA (2018)

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Article Chemistry, Multidisciplinary

Nickel-catalysed decarbonylative borylation of aroyl fluorides

Zhenhua Wang et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Organic

Acid Fluorides as Acyl Electrophiles in Suzuki-Miyaura Coupling

Yohei Ogiwara et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Organic

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

Changhe Zhang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Physical

Acyl Fluorides as Efficient Electrophiles for the Copper-Catalyzed Boroacylation of Allenes

Arnaud Boreux et al.

ACS CATALYSIS (2017)

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Article Chemistry, Physical

Site-Selective C-H/C-N Activation by Cooperative Catalysis: Primary Amides as Arylating Reagents in Directed C-H Arylation

Guangrong Meng et al.

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed Coupling of Benzoyl Halides with Aryltrifluorosilanes Leading to Diaryl Ketones

Yohei Ogiwara et al.

CHEMISTRY LETTERS (2016)

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Article Chemistry, Organic

Acyl Azolium Fluorides for Room Temperature Nucleophilic Aromatic Fluorination of Chloro- and Nitroarenes

Sarah J. Ryan et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones

Lisa Candish et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Article Chemistry, Organic

Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

Julia A. Kalow et al.

TETRAHEDRON (2013)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed (4+2) Cycloaddition/Decarboxylation of Silyl Dienol Ethers with α,β-Unsaturated Acid Fluorides

Sarah J. Ryan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Article Chemistry, Multidisciplinary

Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides

Julia A. Kalow et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual-Catalyst System

Julia A. Kalow et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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N-Heterocyclic Carbene-Catalyzed Generation of α,β-Unsaturated Acyl Imidazoliums: Synthesis of Dihydropyranones by their Reaction with Enolates

Sarah J. Ryan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Review Chemistry, Multidisciplinary

Enantioselective cross-coupling of anhydrides with organozinc reagents: The controlled formation of carbon-carbon bonds through the nucleophilic interception of metalacycles

Jeffrey B. Johnson et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

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Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

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Article Chemistry, Inorganic & Nuclear

Comparing nickel- and palladium-catalyzed Heck reactions

BL Lin et al.

ORGANOMETALLICS (2004)

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Article Chemistry, Multidisciplinary

A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters

YD Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Inorganic & Nuclear

Carbon-fluorine bond activation of perfluorinated arenes with Cp2*ZrH2

BM Kraft et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2002)

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