☆ 4.6 Article

Divergent Fluorinations of Vinylcyclopropanes: Ring-Opening 1,5-Hydrofluorination and Ring-Retaining 1,2-Difluorination

CHEMISTRY-AN ASIAN JOURNAL (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Review Chemistry, Multidisciplinary

Biological Utility of Fluorinated Compounds: from Materials Design to Molecular Imaging, Therapeutics and Environmental Remediation

Cheng Zhang et al.

Summary: This review discusses the applications of fluorinated molecules in bioengineering and nanotechnology, with a focus on controlling fluorine-fluorine interactions and understanding their impact on biological behavior. The controlled introduction of fluorine and its interactions can provide advantages in imaging, therapeutics, and environmental applications.

CHEMICAL REVIEWS (2022)

添加到收藏夹

Article Chemistry, Organic

Oxidative Fluoroarylation of Benzylidenecyclopropanes with HF•Py and Aryl Iodides via Iodonio-[3,3]-Rearrangement

Long-Ling Huang et al.

Summary: This study presents an in situ-generated hypervalent iodine-incorporating fluoroarylation reaction using HF·Py and aryl iodides to react with benzylidenecyclopropanes, providing valuable monofluorinated products for organic synthesis with mild reaction conditions.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine in Medicinal Chemistry: In Perspective to COVID-19

Cheng Zhang

Summary: Researchers have made progress in exploring effective and economical anti-COVID-19 drugs, including fluorinated oral drugs. These drugs can be taken orally at home and used after exposure to the SARS-CoV-2 virus or at the first signs of COVID-19.

ACS OMEGA (2022)

添加到收藏夹

Article Chemistry, Organic

Cyclopropene activation via I(I)/I(III) catalysis: Proof of principle and application in direct tetrafluorination

Stephanie Meyer et al.

Summary: Preliminary validation of cyclopropene activation by an I(I)/I(III) catalysis manifold enables direct tetrafluorination, generating four C(sp(3))-F bonds. A mechanism involving two discrete catalytic processes is proposed, and hypervalent iodine catalysis is added to the strategies for cyclopropene activation.

TETRAHEDRON (2022)

添加到收藏夹

Article Chemistry, Organic

Hypervalent iodine(iii)-mediated ring-expansive difluorination of alkynylcyclopropanes en route to the synthesis of difluorinated alkylidenecyclobutanes

Shuang Yang et al.

Summary: This study presents a new method for the synthesis of difluorinated alkylidenecyclobutanes through a hypervalent iodine(iii)-mediated reaction using commercially available Olah's reagent as the fluorine source. The reaction proceeds under mild conditions and provides moderate to good yields. Mechanistic investigations indicate that the reaction involves regioselective 1,2-fluoroiodination of a triple bond followed by a Wagner-Meerwein-type rearrangement.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Vincent Pirenne et al.

Summary: This review discusses the development of enantioselective methods for the ring opening of cyclopropanes, including reactions based on nonchiral cyclopropanes and asymmetric transformations of chiral substrates. It is organized according to substrate classes, focusing on both established and emerging methods for enantioselective ring opening reactions of different cyclopropanes.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

C-C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Ruben Vicente

Summary: This review summarizes key reactivities relying on C-C bond cleavages of cyclopropenes, including both metal-catalyzed and metal-free transformations. The emphasis is on the synthetic utility and mechanistic aspects of various methodologies discussed, covering a range of reactions involving vinyl carbenes, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, and cycloadditions. The focus is on results from 2007 to 2019, with relevant pioneering transformations eventually included.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Organic

Ring-opening fluorination of cyclopropylmethanols and cycloprpanecarbardehydes with diethylaminosulfur trifluoride

Masayuki Kirihara et al.

Summary: The reaction between cyclopropylmethanols bearing aromatic substituents on their cyclopropane rings and diethylaminosulfur trifluoride (DAST) effectively resulted in ring-opening fluorination to produce homoallylic fluorides. This reaction proceeds via a carbocation intermediate. Moreover, DAST reacted with cyclopropanecarbaldehydes containing electron donating aromatic substituents to cause ring-opening fluorinations with the addition of two fluorine atoms, giving 1,4-difluorobut-1-enes as the final products.

TETRAHEDRON LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2-Alkylidenecyclobutanol Derivatives: Access to β-Monofluorinated Cyclopropanecarbaldehydes

Si-Xin Feng et al.

Summary: A hypervalent iodine(III)-mediated ring-contractive fluorination reaction method was developed for synthesizing beta-monofluorinated cyclopropanecarbaldehydes, with the importance of protecting the free alcohol group highlighted for challenging electron-rich arene substrates. The study demonstrated the synthetic scalability of the reaction and further transformations of the products.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

gem-Difluorination of Methylenecyclopropanes (MCPs) Featuring a Wagner-Meerwein Rearrangement: Synthesis of 2-Arylsubstituted gem-Difluorocyclobutanes

Peng-Peng Lin et al.

Summary: A new method for the synthesis of 2-arylsubstituted gem-difluorocyclobutanes is reported in this study, which exhibits good functional group tolerance and moderate to good yields.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Induced Meerwein Fluoroarylation of Styrenes

Hai-Jun Tang et al.

Summary: An unprecedented approach has been developed for assembling a wide range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers. The key to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and single electron acceptor, enabling a radical-polar crossover manifold.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ring Expansion Fluorination of Unactivated Cyclopropanes Mediated by a New Monofluoroiodane(III) Reagent

Jing Ren et al.

Summary: A new strategy for carbon-carbon bond scission and intramolecular ring expansion fluorination of unactivated cyclopropanes was reported in this study, using a new hypervalent fluoroiodane(III) reagent 1. The reagent, characterized by NMR spectroscopy and X-ray crystallography, was synthesized in three steps with good overall yield and demonstrated high stability due to a secondary I...O bonding interaction. The reaction proceeds via a carbocation intermediate combining with fluoride ion to generate the product, as shown by density functional theory calculations and experimental studies.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Driven Photoredox-Catalyzed Three-Component Radical Cyanoalkylfluorination of Alkenes with Oxime Esters and a Fluoride Ion

Hao Qian et al.

Summary: A metal-free, photoredox-catalyzed three-component cyanoalkylfluorination reaction has been reported, providing a convenient and efficient method for the synthesis of diverse cyanoalkylfluorinated products from readily available substrates under mild and redox-neutral conditions. The protocol shows excellent functional group tolerance and is suitable for cyanoalkylfluorination of pharmaceutically relevant molecule-derived alkenes.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules

Pan Peng et al.

Summary: The study developed a method for electrochemical C-C bond cleavage and 1,3-difunctionalization of arylcyclopropanes under catalyst-free and external-oxidant-free conditions. By strategically choosing nucleophiles, high chemo- and regioselectivity were achieved in reactions involving 1,3-difluorination, 1,3-oxyfluorination and 1,3-dioxygenation.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones

Xi-Jia Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

Ming-Ming Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Organic

Convergent Synthesis of Dihydropyrans from Catalytic Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and Diphenyl Sulfoxide

Ya-Lin Zhang et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Organic

B(C6F5)3-Catalyzed Hydrosilylation of Vinylcyclopropanes

Peng-Wei Long et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Promoted Ir(III)-Catalyzed Z→E Isomerization of Monofluorostilbenes

Qi-Qi Zhang et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic 1,5-trifluoromethylthio-sulfonylation of vinylcyclopropane mediated by visible light in the water phase

Junkai Liu et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

添加到收藏夹

Article Chemistry, Organic

Regio- and Stereoselective Alkenylation of Allenoates with gem-Difluoroalkenes: Facile Access to Fluorinated 1,4-Enynes Bearing an All-Carbon Quaternary Center

Qi-Qi Zhang et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation

Takahide Fukuyama et al.

SCIENCE CHINA-CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

Matthew H. Gieuw et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

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

Yi Zhu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

添加到收藏夹

Article Chemistry, Organic

Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins

Daniel M. Sedgwick et al.

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

gem-Difluorination of Alkenyl N-methyliminodiacetyl Boronates: Synthesis of alpha- and beta-Difluorinated Alkylborons

Wen-Xin Lv et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Fluorine Gauche Effect: A Brief History

Christian Thiehoff et al.

ISRAEL JOURNAL OF CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation

Steven M. Banik et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent

Shuo Guo et al.

NATURE CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination

Nadia O. Ilchenko et al.

CHEMICAL SCIENCE (2017)

添加到收藏夹

Editorial Material Chemistry, Multidisciplinary

Removing the Mask in Catalytic Asymmetric Diamination of Alkenes

Xiao Zhang et al.

CHEM (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate

Cody Ross Pitts et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Difluorination of Olefins

Istvan Gabor Molnar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic, Diastereoselective 1,2-Difluorination of Alkenes

Steven M. Banik et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Site-Selective Approach to -Fluorination: Photocatalyzed Ring Opening of Cyclopropanols

Steven Bloom et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

添加到收藏夹

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ-Fluorinated Ketones

Huijun Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly Selective Pd-Catalyzed Intermolecular Fluorosulfonylation of Styrenes

Zheliang Yuan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Organic

Copper(I)-Catalyzed Intramolecular Trifluoromethylation of Methylenecyclopropanes

Zi-Zhong Zhu et al.

ORGANIC LETTERS (2015)

添加到收藏夹

Article Chemistry, Organic

Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes

Christian Roesner et al.

ORGANIC LETTERS (2015)

添加到收藏夹

Review Chemistry, Inorganic & Nuclear

Successful fluorine-containing herbicide agrochemicals

Tomoya Fujiwara et al.

JOURNAL OF FLUORINE CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct, Catalytic Monofluorination of sp3 C-H Bonds: A Radical-Based Mechanism with Ionic Selectivity

Cody Ross Pitts et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Multiwfn: A multifunctional wavefunction analyzer

Tian Lu et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications

Richard I. McDonald et al.

CHEMICAL REVIEWS (2011)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Stereoselective fluorination of methylenecyclopropanes with N-F reagents: A modular entry to γ-fluorohomoallylic sulfonimides and γ-fluorohomoallylic amides

Weijun Fu et al.

JOURNAL OF FLUORINE CHEMISTRY (2009)

添加到收藏夹

Review Chemistry, Physical

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions

Aleksandr V. Marenich et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2009)

添加到收藏夹

Article Chemistry, Organic

Reactions of methylenecyclopropanes and vinylidenecyclopropanes with N-fluorodibenzenesulfonimide

Min Jiang et al.

TETRAHEDRON (2009)

添加到收藏夹

Editorial Material Chemistry, Medicinal

The many roles for fluorine in medicinal chemistry

William K. Hagmann

JOURNAL OF MEDICINAL CHEMISTRY (2008)

添加到收藏夹

Article Chemistry, Physical

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals

Yan Zhao et al.

THEORETICAL CHEMISTRY ACCOUNTS (2008)

添加到收藏夹

Review Chemistry, Multidisciplinary

C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents

Egle M. Beccalli et al.

CHEMICAL REVIEWS (2007)

添加到收藏夹

Review Multidisciplinary Sciences

Fluorine in pharmaceuticals:: Looking beyond intuition

Klaus Mueller et al.

SCIENCE (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation

Takeo Fukuzumi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of potent thiosemicarbazone inhibitors of rhodesain and cruzain

N Fujii et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2005)

添加到收藏夹

Review Chemistry, Multidisciplinary

Selectfluor: Mechanistic insight and applications

PT Nyffeler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.