Transition‐Metal‐Catalyzed Monofluoroalkylation: Strategies for the Synthesis of Alkyl Fluorides by C−C Bond Formation

Cobalt-catalyzed synthesis of bromomonofluoroallyl ketones by addition of alkynes and α-bromo-α-fluoroketones

(2021) Jie Ren et al.   TETRAHEDRON LETTERS

Diversity‐Oriented Synthesis of Aliphatic Fluorides via Reductive C(sp3)–C(sp3) Cross‐Coupling Fluoroalkylation

(2021) Jie Sheng et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Effects of Replacing Oxygenated Functionality with Fluorine on Lipophilicity

(2021) Richard J. Glyn et al.   JOURNAL OF MEDICINAL CHEMISTRY

Reagents for Selective Fluoromethylation - a Challenge in Organofluorine Chemistry

(2020) Marco Reichel et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Direct Copper-Catalyzed C-H Monofluoroalkylation of Benzoxazoles with 1-Fluoro-1-haloalkanes

(2020) Wei Li et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Cobalt‐Catalyzed α‐Arylation of Substituted α‐Bromo α‐Fluoro β‐Lactams with Diaryl Zinc Reagents. Generalization to Functionalized Bromo Derivatives.

(2020) Melanie Marie Lorion et al.   CHEMISTRY-A EUROPEAN JOURNAL

Desymmetrization of difluoromethylene groups by C–F bond activation

(2020) Trevor W. Butcher et al.   NATURE

Cobalt-Catalyzed Asymmetric Cross-Coupling Reaction of Fluorinated Secondary Benzyl Bromides with Lithium Aryl Boronates/ZnBr2

(2020) Weichen Huang et al.   ORGANIC LETTERS

Engaging α-Fluorocarboxylic Acids Directly in Decarboxylative C–C Bond Formation

(2020) Hongyu Wang et al.   ACS Catalysis

The role of fluorine in glycomimetic drug design

(2020) Rachel Hevey   CHEMISTRY-A EUROPEAN JOURNAL

Copper-Catalyzed Defluorinative Borylation and Silylation of gem-Difluoroallyl Groups

(2020) Trevor W. Butcher et al.   ORGANIC LETTERS

Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis

(2019) Agostinho Lemos et al.   ADVANCED SYNTHESIS & CATALYSIS

Synthesis of Polyfunctionalised 2-Piperidinones Catalysed by Fe(acac)3

(2019) Eric Talbot   SYNLETT

The fluorination of C-H bonds: developments and perspectives

(2019) Veronique Gouverneur et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Iridium-Catalyzed Asymmetric Synthesis of Functionally Rich Molecules Enabled by (Phosphoramidite,Olefin) Ligands

(2019) Simon L. Rössler et al.   ACCOUNTS OF CHEMICAL RESEARCH

Mechanism and Origin of Enantioselectivity in Nickel-Catalyzed Alkyl–Alkyl Suzuki Coupling Reaction

(2019) Sukriti Singh et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts

(2019) Zhi-Tao He et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective construction of remote tertiary carbon–fluorine bonds

(2019) Jianbo Liu et al.   Nature Chemistry

Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides

(2019) Jonathan M. E. Hughes et al.   ORGANIC LETTERS

Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

(2019) Junqing Liang et al.   ORGANIC LETTERS

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

(2019) Xin Wang et al.   ORGANIC LETTERS

Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile

(2019) Hiroaki Tsuji et al.   ORGANIC LETTERS

Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

(2019) Masakazu Nambo et al.   Nature Communications

Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones

(2019) Xi-Jia Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation

(2018) Jie Sheng et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs

(2018) Feipeng Liu et al.   CHEMISTRY-A EUROPEAN JOURNAL

Palladium-Catalyzed Asymmetric Allylic Alkylations of Colby Pro-Enolates with MBH Carbonates: Enantioselective Access to Quaternary C−F Oxindoles

(2018) Yi Zhu et al.   CHEMISTRY-A EUROPEAN JOURNAL

Nickel-Catalyzed Heck-Type Monofluoroacetation of Styrenes for Facile Synthesis of Allylic Fluorides

(2018) Zhen-Yu Wang et al.   Chemistry-An Asian Journal

Diastereoselective and Enantioselective Palladium-Catalyzed Allylic Substitution of Substituted Fluorinated Methylene Derivatives

(2018) Tao Song et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Modular radical cross-coupling with sulfones enables access to sp3-rich (fluoro)alkylated scaffolds

(2018) Rohan R. Merchant et al.   SCIENCE

Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of β-Fluoro Michael Acceptors

(2018) Thomas J. O’Connor et al.   ACS Catalysis

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

(2018) Jing Yang et al.   Catalysts

Transition-Metal (Cu, Pd, Ni)-Catalyzed Difluoroalkylation via Cross-Coupling with Difluoroalkyl Halides

(2018) Zhang Feng et al.   ACCOUNTS OF CHEMICAL RESEARCH

Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation

(2018) Trevor W. Butcher et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Iron–Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers

(2018) Samantha A. Green et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-Catalyzed Enantioselective Csp3–Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks

(2018) Yanhui Lu et al.   ORGANIC LETTERS

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

(2018) Qiang Cheng et al.   CHEMICAL REVIEWS

Irradiation-Induced Cobaloxime-Catalyzed C–H Monofluoroalkylation of Styrenes at Room Temperature

(2018) Wei-Ke Tang et al.   ORGANIC LETTERS

Mechanistic Study of an Improved Ni Precatalyst for Suzuki–Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species

(2017) Megan Mohadjer Beromi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Tertiary Sulfones

(2017) Zachary T. Ariki et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-catalyzed synthesis of monofluoroalkenes from 3,3-difluoropropenes using dimethylmalonate and derivatives as nucleophiles

(2017) Myriam Drouin et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles

(2017) Yushu Jin et al.   ORGANIC LETTERS

Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides

(2017) Tingting Xia et al.   ORGANIC LETTERS

Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides

(2017) Jie Sheng et al.   ORGANIC LETTERS

Copper-Mediated Synthesis of Monofluoro Aryl Acetates via Decarboxylative Cross-Coupling

(2017) Rylan Lundgren et al.   SYNLETT

Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes

(2016) Richard T. Thornbury et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles

(2016) Kaluvu Balaraman et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

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

(2016) Yu Zhou et al.   CHEMICAL REVIEWS

Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones

(2016) Zhiwei Jiao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Metallaphotoredox-catalysed sp3–sp3 cross-coupling of carboxylic acids with alkyl halides

(2016) Craig P. Johnston et al.   NATURE

Enantioselective synthesis of fluorinated branched allylic compounds via Ir-catalyzed allylations of functionalized fluorinated methylene derivatives

(2016) Hongbo Zhang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Stereospecific Synthesis of Tri- and Tetrasubstituted α-Fluoroacrylates by Mizoroki–Heck Reaction

(2016) Kevin Rousée et al.   ORGANIC LETTERS

Exploiting a Difference in Leaving Group Ability: An Approach to β-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes

(2016) Jean-Denys Hamel et al.   ORGANIC LETTERS

Nickel-Catalyzed Monofluoroalkylation of Arylsilanes via Hiyama Cross-Coupling

(2016) Yun Wu et al.   ORGANIC LETTERS

Cu-catalyzed hydrofluoroacetylation of alkynes or alkynyl carboxylic acids leading highly stereoselectively to fluoroacetylated alkenes

(2016) Miaolin Ke et al.   Organic Chemistry Frontiers

Advances in Transition-Metal-Mediated Di-and Monofluoroalkylations

(2015) Chuanfa Ni et al.   ACTA CHIMICA SINICA

Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)

(2015) Louise M. Guard et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Monofluoromethylation of Aryl Boronic Acids

(2015) Yi-Ming Su et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Monofluorination of Organic Compounds: 10 Years of Innovation

(2015) Pier Alexandre Champagne et al.   CHEMICAL REVIEWS

Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

(2015) Alan H. Cherney et al.   CHEMICAL REVIEWS

Synthesis of monofluoroalkenes using a Pt-catalyzed amination reaction of cyclic 3,3-difluoropropenes with secondary aliphatic amines

(2015) Jean-Denys Hamel et al.   JOURNAL OF FLUORINE CHEMISTRY

Applications of Fluorine in Medicinal Chemistry

(2015) Eric P. Gillis et al.   JOURNAL OF MEDICINAL CHEMISTRY

Enantioselective Suzuki Cross-Couplings of Unactivated 1-Fluoro-1-haloalkanes: Synthesis of Chiral β-, γ-, δ-, and ε-Fluoroalkanes

(2015) Xiaojian Jiang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides

(2015) Adam Noble et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective synthesis of monofluorinated allylic compounds: Pd-catalyzed asymmetric allylations of dimethyl 2-fluoromalonate using new N-sulfinyl-based ligands

(2015) Ning Gao et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

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

(2014) Xiaoyu Yang et al.   CHEMICAL REVIEWS

Successful fluorine-containing herbicide agrochemicals

(2014) Tomoya Fujiwara et al.   JOURNAL OF FLUORINE CHEMISTRY

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

(2014) Wei Zhu et al.   JOURNAL OF FLUORINE CHEMISTRY

Enantioselective Pd-Catalyzed Allylation of Acyclic α-Fluorinated Ketones

(2014) Wengui Wang et al.   JOURNAL OF ORGANIC CHEMISTRY

Efficient Synthesis of Secondary Alkyl Fluorides via Suzuki Cross-Coupling Reaction of 1-Halo-1-fluoroalkanes

(2014) Xiaojian Jiang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones

(2014) Yufan Liang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cobalt–Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-Bromo Esters with Aryl Grignard Reagents

(2014) Jianyou Mao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly Selective gem-Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium

(2014) Qiao-Qiao Min et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Functionalized olefin cross-coupling to construct carbon–carbon bonds

(2014) Julian C. Lo et al.   NATURE

Merging photoredox with nickel catalysis: Coupling of  -carboxyl sp3-carbons with aryl halides

(2014) Z. Zuo et al.   SCIENCE

Review of recent advances in nucleophilic C–F bond-forming reactions at sp3 centers

(2014) Jimmy Wu   TETRAHEDRON LETTERS

The influence of fluorine in asymmetric catalysis

(2013) Dominique Cahard et al.   CHEMICAL SOCIETY REVIEWS

Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

(2013) Scott E. Denmark et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters

(2013) Wen-Bo Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Copper-Catalyzed Debenzoylative Monofluoromethylation of Aryl Iodides Assisted by the Removable (2-Pyridyl)sulfonyl Group

(2013) Yanchuan Zhao et al.   ACS Catalysis

Silver-Assisted Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of Bromofluoroalkenes

(2012) Yibiao Li et al.   ADVANCED SYNTHESIS & CATALYSIS

Aromatic Spiroketal Bisphosphine Ligands: Palladium-Catalyzed Asymmetric Allylic Amination of Racemic Morita-Baylis-Hillman Adducts

(2012) Xiaoming Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Kumada Reaction of Tosylalkanes with Grignard Reagents to Produce Alkenes and Modified Arylketones

(2012) Ji-Cheng Wu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis of 3-Fluoro-3-aryl Oxindoles: Direct Enantioselective α Arylation of Amides

(2012) Linglin Wu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

In VitroActivity of the New Fluoroketolide Solithromycin (CEM-101) against a Large Collection of Clinical Neisseria gonorrhoeae Isolates and International Reference Strains, Including Those with High-Level Antimicrobial Resistance: Potential Treatment Option for Gonorrhea?

(2012) Daniel Golparian et al.   ANTIMICROBIAL AGENTS AND CHEMOTHERAPY

Iridium-Catalyzed Allylic Alkylation Reaction with N-Aryl Phosphoramidite Ligands: Scope and Mechanistic Studies

(2012) Wen-Bo Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents

(2012) Jörg T. Binder et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A new entry to the construction of a quaternary carbon center having a fluorine atom – SN2′ reaction of γ-fluoroallylic alcohol derivatives with various cyanocuprates

(2012) Tsutomu Konno et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group

(2012) Yanchuan Zhao et al.   ORGANIC LETTERS

Ni-catalyzed α-arylation of secondary α-bromo-α-fluoro-β-lactam: cross-coupling of a secondary fluorine-containing electrophile

(2012) Atsushi Tarui et al.   TETRAHEDRON

Palladium-catalyzed direct α-arylation of α-fluoroketones: A straightforward route to α-fluoro-α-arylketones

(2011) Chen Guo et al.   JOURNAL OF FLUORINE CHEMISTRY

Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design

(2011) Nicholas A. Meanwell   JOURNAL OF MEDICINAL CHEMISTRY

Design, Synthesis, and Applications of Potential Substitutes of t-Bu-Phosphinooxazoline in Pd-Catalyzed Asymmetric Transformations and Their Use for the Improvement of the Enantioselectivity in the Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates

(2011) Étienne Bélanger et al.   JOURNAL OF ORGANIC CHEMISTRY

Mizoroki–Heck Reaction of (1-Fluorovinyl)methyldiphenylsilane with Aryl Iodides

(2011) Kensuke Hirotaki et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams

(2011) Douglas C. Behenna et al.   Nature Chemistry

Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution

(2010) John F. Hartwig et al.   ACCOUNTS OF CHEMICAL RESEARCH

Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position

(2010) Feng Zhou et al.   ADVANCED SYNTHESIS & CATALYSIS

Metal-Catalyzed α-Arylation of Carbonyl and Related Molecules: Novel Trends in CC Bond Formation by CH Bond Functionalization

(2010) Carin C. C. Johansson et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones

(2010) Sha Lou et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Impact of Silyl Enol Ether Stability on Palladium-Catalyzed Arylations

(2010) Yong Guo et al.   ORGANOMETALLICS

Activation of Allylic CF bonds: Palladium-Catalyzed Allylic Amination of 3,3-Difluoropropenes

(2009) Xavier Pigeon et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

C−F Bond Activation in Organic Synthesis

(2009) Hideki Amii et al.   CHEMICAL REVIEWS

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

(2009) Fabio Bellina et al.   CHEMICAL REVIEWS

Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

(2009) Frank Lovering et al.   JOURNAL OF MEDICINAL CHEMISTRY

Pd-catalyzed arylation of silyl enol ethers of substituted α-fluoroketones

(2009) Yong Guo et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Use of 5,5-(Dimethyl)-i-Pr-PHOX as a Practical Equivalent tot-Bu-PHOX in Asymmetric Catalysis

(2009) Étienne Bélanger et al.   ORGANIC LETTERS

Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

(2008) Étienne Bélanger et al.   CHEMICAL COMMUNICATIONS

Heck reaction with 3-fluoro-3-buten-2-one

(2008) Timothy B. Patrick et al.   JOURNAL OF FLUORINE CHEMISTRY

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

(2007) David O'Hagan   CHEMICAL SOCIETY REVIEWS

Fluorine in medicinal chemistry

(2007) Sophie Purser et al.   CHEMICAL SOCIETY REVIEWS