4.7 Article

Photocatalytic Decarboxylative Coupling of Aliphatic N-Hydroxyphthalimide Esters with Bromopolyfluorobenzene

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Fluorine-containing drugs approved by the FDA in 2021

Jingrui He et al.

Summary: This review article presents nine newly approved fluorine-containing drugs by the US Food and Drug Administration (FDA) in 2021. These small molecule drugs feature aromatic fluo-rine, trifluoromethyl, and chlorodifluoro groups. The therapeutic areas of these fluorine-containing drugs include multiple myeloma, lymphoma, HIV, chronic heart failure, chronic myeloid leukemia, (ANCA)-associated vasculitis, migraines, von Hippel-Lindau disease, and non-small cell lung cancer. The review also discusses the brief biological activities and synthetic methods for each of these nine drugs.

CHINESE CHEMICAL LETTERS (2023)

Review Chemistry, Multidisciplinary

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Amy Y. Chan et al.

Summary: The merger of photoredox catalysis with transition metal catalysis, known as metallaphotoredox catalysis, has become an important part of synthetic methodology. It combines the bond formation capability of transition metal catalysis with the utility of photoinduced electron and energy transfer processes. Photocatalytic substrate activation allows the involvement of simple starting materials in metal-mediated bond-forming processes, while electron or energy transfer with organometallic intermediates provides a complementary activation mode to traditional catalytic platforms.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

Photoredox Polyfluoroarylation of Alkyl Halides via Halogen Atom Transfer

Ben Niu et al.

Summary: Here, we report the first polyfluoroarylation of unactivated alkyl halides via a halogen atom transfer process. This method shows good yields in converting primary, secondary, and tertiary alkyl halides into the respective polyfluoroaryl compounds, including derivatives of complex bioactive molecules.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Nickel-Catalyzed Cross-Coupling of Amino-Acid-Derived Alkylzinc Reagents with Alkyl Bromides/Chlorides: Access to Diverse Unnatural Amino Acids

Fei-Hu Gou et al.

Summary: The study presents an efficient, versatile, and straightforward strategy for the synthesis of homophenylalanine derivatives via nickel-catalyzed Csp(3)-Csp(3) cross-coupling. The method features a low-cost nickel catalyst system, synthetic convenience, and tolerance of rich functionality and stereochemistry.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Visible-light-induced direct 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles in water

Chun-Hua Ma et al.

Summary: A novel visible-light-driven catalytic reaction has been developed for the 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles and imidazo[1,2-a]pyridines using commercially available alpha-bromoesters in water. This protocol offers sustainability, ease of operation, mild reaction conditions, and a wide range of applicable substrates, including alpha-bromoamides for 3-carbamylmethylation products. It has potential applications in drug synthesis like zolpidem and late-stage modification of natural products.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Direct benzylation reactions from benzyl halides enabled by transition-metal-free photocatalysis

Panjie Xiang et al.

Summary: An S(N)2-based photochemical strategy using dithiocarbamate anion as catalyst has been developed for the activation of benzyl halides, allowing the benzylation (or cyanomethylation) of various heterocycles with high yields. This transition-metal-free and oxidant-free protocol also enables the synthesis of biologically relevant compounds under mild conditions.

CHINESE CHEMICAL LETTERS (2022)

Article Chemistry, Organic

Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor

Peng Guo et al.

Summary: This study reports the first example of using commercially available 2-bromo-3,3,3-trifluoropropene as a radical acceptor to synthesize secondary trifluoromethylated alkyl bromides. The practicality of this method was further demonstrated by diverse derivations and direct modification of biologically active molecules.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Recent advances in photocatalytic polyfluoroarylation

Yan Liu et al.

Summary: Polyfluoroaryl compounds have distinct properties and are widely used in pharmaceuticals, agrochemicals, and materials. Photocatalytic polyfluoroarylation using polyfluoroarenes as radical precursors has become a hot topic in chemical research. This review presents the state-of-the-art in photocatalytic polyfluoroarylation since 2014, covering the basic concept, reaction design, mechanistic insight, and research prospects.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids

Xiang Sun et al.

Summary: In this study, a novel method for polyfluoroarylation of aliphatic carboxylic acids was reported, with broad substrate scope and high functional group tolerance. Small complex molecules such as natural products and drugs can be modified through late-stage modification.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Palladium-Catalysed C-H Bond Zincation of Arenes: Scope, Mechanism, and the Role of Heterometallic Intermediates

Marti Garcon et al.

Summary: This study demonstrates a new method of transforming C-H bonds into C-Zn bonds using a palladium catalyst and zinc hydride reagent, which has been successfully applied to various types of arenes with high selectivity. Mechanistic studies show that heterometallic complexes play a crucial role in the catalytic process.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity

Yingjie Yu et al.

Summary: This review profiles thirteen new fluorine-containing drugs recently approved by the US FDA in 2020, covering a range of therapeutic areas including Alzheimer's disease, migraine, and various cancers. The approved drugs feature different types of fluorine groups, such as aromatic fluorine (Ar-F), aromatic Ar-CF3, aliphatic CHF and CF2. For each compound, the review provides details on biological activity, medicinal chemistry discovery, and synthetic approaches.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Organic

Lewis Acid Activation of Fragment-Coupling Reactions of Tertiary Carbon Radicals Promoted by Visible-Light Irradiation of EDA Complexes

Spencer P. Pitre et al.

Summary: The addition of tertiary carbon radicals from N-(acyloxy)phthalimide esters to cyclic alpha, beta-unsaturated ketones and lactones is greatly enhanced by substoichiometric amounts of Ln(OTf)(3). The reaction, which does not require a photosensitizer, is suggested to proceed through excitation of a ternary electron donor-acceptor complex between the NHPI ester, Hantzsch ester, and Ln(OTf)(3).

ORGANIC LETTERS (2021)

Review Chemistry, Physical

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Sushanta Kumar Parida et al.

Summary: NHPI esters and their derivatives have emerged as a forefront in synthetic methods, undergoing reductive fragmentation to generate radicals for diverse synthetic transformations. They are widely applicable in cascade annulations as well as medicinal chemistry and natural product synthesis. This review categorizes the progress in this field according to bond formation nature, providing representative examples with mechanistic details and highlighting challenges and future directions.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Late-Stage Alkylation of Heterocycles Using N-(Acyloxy)phthalimides

Sushanta Kumar Parida et al.

Summary: Synthetic methods enabling late-stage modification of heterocycles are crucial in the pharmaceutical and agrochemical industry. The development of catalysts has made C-H alkylation of heterocycles more accessible and efficient, leading to significant breakthroughs in medicinal chemistry.

CHEMISTRY-AN ASIAN JOURNAL (2021)

Review Chemistry, Applied

Utilization of C(sp3)-Carboxylic Acids and Their Redox-Active Esters in Decarboxylative Carbon-Carbon Bond Formation

Sukhen Karmakar et al.

Summary: In recent years, radical-mediated decarboxylative cross-coupling reactions using alkyl carboxylic acids have become a powerful tool for constructing carbon-carbon bonds, leading to complex chemical scaffolds. This synthetic strategy has advantages over conventional organometallic reagents in terms of abundant starting material availability and high functional group tolerance.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Organic

Cu-Catalyzed Direct C-H Alkylation of Polyfluoroarenes via Remote C(sp3)-H Functionalization in Carboxamides

Hong-Chao Liu et al.

Summary: A novel dehydrogenative coupling reaction of N-fluorocarboxamides with polyfluoroarenes forming C(sp(2))-C(sp(3)) bonds enabled by copper catalysis has been accomplished, demonstrating excellent regioselectivity and supported by control experiments and density functional theory calculations.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Xiangli Yi et al.

Summary: The study presents a decarboxylative coupling reaction using photoredox and copper catalysis to convert alkyl carboxylic acids into polyfluoroaryl compounds. The method demonstrates broad scope and good functional group compatibility, with the potential to achieve a wide range of F-substitution patterns on the aryl groups. Mechanistic study suggests a [Cu-(Ar-F)(2)] species may be responsible for the transfer of polyfluoroaryl groups to alkyl radicals.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Visible light induced deaminative alkylation of difluoroenoxysilanes: a transition metal free strategy

Qi-Ping Huang et al.

Summary: Hantzsch ester acts as a catalyst in the deaminative difluoroalkylation reaction, representing a rare example of electron donor-acceptor photochemistry. A substrate-induced pathway was observed, especially for substrates derived from amino acids. This mild and convenient approach provides a valuable method for installing a diverse range of alkyl-CF2COPh products.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp3)-C(sp2) bond formation

Lisa Marie Kammer et al.

Summary: A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp(3))-C(sp(2)) linkages has been developed. This platform utilizes commercially available Hantzsch ester as an organic photoreductant to generate catalytically active Ni(0) species under light irradiation, enabling the coupling of diverse C(sp(3))-centered radical architectures with (hetero)aryl bromides. The protocol proceeds under mild reaction conditions and is compatible with sensitive functional groups and pharmaceutically relevant cores.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

Fluorine-containing drugs approved by the FDA in 2019

Haibo Mei et al.

CHINESE CHEMICAL LETTERS (2020)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using Hydrocarbons as an Alkylating Source

Weilong Xie et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Organic

One-Electron Reduction of Redox-Active Esters to Generate Carbon-Centered Radicals

Pengfei Niu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes

Xiaohong Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C-H Arylation

Weilong Xie et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Dual Catalytic Strategy for Forging sp2-sp3 and sp3-sp3 Architectures via β-Scission of Aliphatic Alcohol Derivatives

Fei Cong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides

Tiffany Q. Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling

John A. Milligan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Review Chemistry, Applied

N-(Acyloxy)phthalimides as Redox-Active Esters in Cross-Coupling Reactions

Sandip Murarka

ADVANCED SYNTHESIS & CATALYSIS (2018)

Review Agronomy

Latest generation of halogen-containing pesticides

Peter Jeschke

PEST MANAGEMENT SCIENCE (2017)

Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Donor-Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)-C(sp3) Cleavage and Allylation/Alkenylation

Jing Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

[Cu(NHC)]-Catalyzed C-H Allylation and Alkenylation of both Electron-Deficient and Electron-Rich (Hetero)arenes with Allyl Halides

Weilong Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides

Marco Simonetti et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

Patricia Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides

Xiaheng Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct C-H Bond Functionalization

Shuai Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Photocatalytic C-F alkylation; facile access to multifluorinated arenes

A. Singh et al.

CHEMICAL SCIENCE (2015)

Review Chemistry, Multidisciplinary

Fluorinated Proteins: From Design and Synthesis to Structure and Stability

E. Neil G. Marsh

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Article Chemistry, Organic

C-F activation and functionalization of perfluoro- and polyfluoroarenes

Jimmie Weaver et al.

TETRAHEDRON (2014)

Article Chemistry, Organic

Pd-catalyzed aerobic direct olefination of polyfiuoroarenes

Chun-Yang He et al.

TETRAHEDRON LETTERS (2014)

Review Chemistry, Multidisciplinary

Exploring and Exploiting Polar-π Interactions with Fluorinated Aromatic Amino Acids

Christopher J. Pace et al.

ACCOUNTS OF CHEMICAL RESEARCH (2013)

Article Chemistry, Multidisciplinary

Direct Construction of Quaternary Carbons from Tertiary Alcohols via Photoredox-Catalyzed Fragmentation of tert-Alkyl N-Phthalimidoyl Oxalates

Gregory L. Lackner et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Organic

Thioether-Promoted Direct Olefination of Polyfluoroarenes Catalyzed by Palladium

Cai-Zhi Wu et al.

ORGANIC LETTERS (2013)

Review Chemistry, Multidisciplinary

Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions

Mario Salwiczek et al.

CHEMICAL SOCIETY REVIEWS (2012)

Review Biochemistry & Molecular Biology

Fluorine: A new element in protein design

Benjamin C. Buer et al.

PROTEIN SCIENCE (2012)

Article Chemistry, Multidisciplinary

Stereospecific Copper-Catalyzed C-H Allylation of Electron-Deficient Arenes with Allyl Phosphates

Tomoyuki Yao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Direct Palladium-Catalyzed Intermolecular Allylation of Highly Electron-Deficient Polyfluoroarenes

Shilu Fan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Organic fluorine compounds: a great opportunity for enhanced materials properties

Ricarda Berger et al.

CHEMICAL SOCIETY REVIEWS (2011)

Article Chemistry, Multidisciplinary

Direct Pd-catalyzed benzylation of highly electron-deficient perfluoroarenes

Shilu Fan et al.

CHEMICAL COMMUNICATIONS (2010)

Article Chemistry, Inorganic & Nuclear

Hydrofluoroarylation of alkynes with fluoroarenes

Kyalo Stephen Kanyiva et al.

DALTON TRANSACTIONS (2010)

Article Chemistry, Multidisciplinary

Pd(OAc)2 Catalyzed Olefination of Highly Electron-Deficient Perfluoroarenes

Xingang Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles

Chun-Yang He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Rh(I)-Catalyzed Olefin Hydroarylation with Electron-Deficient Perfluoroarenes

Zhong-Ming Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O2 as an Oxidant

Ye Wei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Pd(OAc)2-Catalyzed Oxidative C-H/C-H Cross-Coupling of Electron-Deficient Polyfluoroarenes with Simple Arenes

Ye Wei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Aryl Iodides and Bromides

Rui Shang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Multidisciplinary

Effect of Highly Fluorinated Amino Acids on Protein Stability at a Solvent-Exposed Position on an Internal Strand of Protein G B1 Domain

Hsien-Po Chiu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds

Hien-Quang Do et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom

Francesco Babudri et al.

CHEMICAL COMMUNICATIONS (2007)

Article Chemistry, Multidisciplinary

Catalytic intermolecular direct arylation of perfluorobenzenes

Marc Lafrance et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Organic

Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

T Korenaga et al.

ORGANIC LETTERS (2005)

Review Chemistry, Multidisciplinary

Fluorine in crystal engineering - the little atom that could

K Reichenbacher et al.

CHEMICAL SOCIETY REVIEWS (2005)

Review Chemistry, Multidisciplinary

Interactions with aromatic rings in chemical and biological recognition

EA Meyer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

Review Chemistry, Multidisciplinary

Fluorinated amino acids in protein design and engineering

NC Yoder et al.

CHEMICAL SOCIETY REVIEWS (2002)

Article Chemistry, Multidisciplinary

Catalytic system for heck reactions involving insertion into Pd-(perfluoro-organyl) bonds

AC Albéniz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)