Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF3SO2Na: facile access to α,β-bistrifluoromethyl tertiary alcohols

Review Chemistry, Applied

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

Feng Zhao et al.

Summary: This review summarizes the recent developments of new methods for the synthesis of difluoromethyl motifs or difluoroalkenes from trifluoromethylated aromatic compounds or trifluoromethyl alkenes via single C(sp(3))-F bond cleavage.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Advances in cycloaddition and hydroaddition reaction of α-(trifluoromethyl)styrenes without defluorination: An alternative approach to CF3-containing compounds

Yupian Deng et al.

Summary: Alpha-(trifluoromethyl)styrene and its derivatives are widely used in pharmaceuticals, agrochemicals, and advanced materials. They are versatile building blocks for the preparation of various compounds. Recent efforts have focused on developing reactions for accessing gem-difluoroalkenes and gem-difluoroalkylated compounds without defluorination. However, the use of alpha-(trifluoromethyl)styrenes in cycloaddition and hydroaddition reactions while retaining three C-F bonds remains underdeveloped.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Tunable photocatalytic oxysulfonylation and chlorosulfonylation of α-CF3 alkenes with sulfonyl chlorides

Peng-Ju Xia et al.

Summary: This strategy utilizes tunable photoredox catalysis and manipulation of catalyst and solvent to achieve chlorosulfonylation and oxysulfonylation of alpha-trifluoromethylstyrenes, resulting in diverse bifunctional products with up to 95% yield and excellent functional group tolerance.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Review Chemistry, Multidisciplinary

Application of Langlois' reagent (NaSO2CF3) in C-H functionalisation

Jiabin Shen et al.

Summary: This review provides an overview of the recent advances in the selective introduction of CF3 group into organic molecules using solid sodium trifluoromethanesulfinate. The eco-friendly and cost-effective nature of this method has made it a valuable tool for organic chemists in synthesizing various natural and bioactive compounds.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

DBN-Mediated Addition Reaction of α-(Trifluoromethyl)styrenes with Diazoles, Triazoles, Tetrazoles, and Primary, Secondary, and Secondary Cyclic Amines

Jingjing He et al.

Summary: A mild and efficient DBN-mediated addition reaction was developed for the synthesis of various β-trifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines using α-(trifluoromethyl)styrenes and diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines.

ORGANIC LETTERS (2022)

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Article Chemistry, Physical

Nickel-Catalyzed anti-Markovnikov Hydroalkylation of Trifluoromethylalkenes

Chuan Zhu et al.

Summary: Transition-metal-catalyzed difunctionalization of olefins is a powerful method to access complex molecules from bulk chemicals. In this study, a hydroalkylation reaction of trifluoromethylalkenes with alkyl halides under nickel catalysis was developed, leading to the efficient construction of 1,1,1-trifluoropropane derivatives. The commonly observed beta-fluoride elimination pathway was suppressed by using a competent proton donor, enabling the use of substrates featuring fluoroalkyl substituents.

ACS CATALYSIS (2022)

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Article Chemistry, Physical

Reductive quenching-initiated catalyst-controlled divergent alkylation of α-CF3-olefins

Yunxiao Zhang et al.

Summary: This research demonstrates a visible-light-induced photo-catalyst strategy for preparing both gem-difluoroalkenes and trifluoromethyl alkanes from alpha-CF3-olefins. The selectivity of the reactions depends on the choice of catalyst rather than the modification of substrate structures.

CHEM CATALYSIS (2022)

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Article Chemistry, Organic

Solvent-controlled base-free synthesis of bis(trifluoromethyl)-cyclopropanes and -pyrazolines via cycloaddition of 2-trifluoromethyl-1,3-enynes with 2,2,2-trifluorodiazoethane

Zhihong Ma et al.

Summary: A highly efficient solvent-controlled synthesis of bis(trifluoromethyl)cyclopropanes and bis(trifluoromethyl)pyrazolines was developed. The reactions proceeded smoothly under transition-metal and base-free conditions, affording the expected products in good yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Et3N-Catalyzed Cycloaddition Reactions of α-(Trifluoromethyl)styrenes with 2,2,2-Trifluorodiazoethane to Access Bis(trifluoromethyl)-Substituted Pyrazolines

Chunmei Li et al.

Summary: A novel and practical method for the synthesis of 3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazoles using [3+2] cycloaddition reactions has been developed, achieving good to excellent yields and exhibiting a broad substrate scope with tolerance to various functional groups.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines

Kai Wang et al.

Summary: An eco-friendly and effective electrochemical process using CF3SO2Na as the trifluoromethyl source was developed for the ortho-trifluoromethylation of arylamines, resulting in moderate to good yields with high regioselectivity under mild conditions. The method avoids the use of transition metals and oxidants, proposing a radical mechanism based on various control experiments.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Organic

Dual Roles of TBHP-Enabled Regioselective Hydroetherification of (Trifluoromethyl)alkenes with Boronic Acids: Access to α-Trifluoromethyl β-Aryloxy Tertiary Alcohols

Hengyuan Li et al.

Summary: The study reports a three-starting materials four-component reaction of (trifluoromethyl)alkenes, TBHP, and boronic acids, which delivers various useful alpha-trifluoromethyl-beta-aryloxy tertiary alcohols in high yields and in an exclusively regioselective hydroetherification manner. TBHP serves multiple roles in this reaction, functioning as both the oxidant and nucleophile, as well as the O-source of the products.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Organic

Visible-Light-Induced Trifluoromethylation of Allylic Alcohols

Bowen Li et al.

Summary: An organic photoredox-catalyzed dehydroxylative trifluoromethylation of allylic alcohols was developed in an environmentally friendly manner. The reaction utilized CF3SO2Na as the trifluoromethylation reagent and reutilized the byproduct SO2 to activate C-OH bond, allowing for convenient performance of the dehydroxylative trifluoromethylation and obtaining a variety of multifunctionalized CF3-allylic compounds in high yields and excellent stereoselectivity.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Synthesis of CF3-Containing Linear Nitriles from α-(Trifluoromethyl)styrenes

Sixue Xu et al.

Summary: Four unprecedented base-catalyzed/mediated nucleophilic additions of TMSCN to alpha-(trifluoromethyl)styrenes and 2-trifluoromethyl enynes have been developed. The reaction proceeds smoothly at room temperature under mild and transition-metal-free conditions, affording the corresponding CF3-containing alkyl, alkynyl, and butadienyl nitriles in a highly regioselective manner with moderate to excellent yields.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Yi-Xuan Chen et al.

Summary: This study presents a visible-light-induced sulfonation reaction of alpha-trifluoromethylstyrenes with sodium sulfinates to afford a series of important organic compounds. The protocol features broad substrate scope, excellent chemoselectivity, and is suitable for synthesizing pharmaceutically relevant molecules. Additionally, deuteriotrifluorinated products can be obtained in the presence of D2O, showcasing the flexibility and synthetic potential of this strategy.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Electrochemical heterodifunctionalization of α-CF3 alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

Zhi-Peng Ye et al.

Summary: An unprecedented electrochemical heterodifunctionalization of alpha-CF3 alkenes with benzenesulfonyl hydrazides was achieved in this work, leading to the assembly of a series of potentially medicinally valuable and densely functionalized compounds under mild conditions. This protocol is more eco-friendly by obviating the need for oxidizing reagents in the electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes

Jinwon Jeon et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Visible-light-promoted photocatalyst- and additive-free intermolecular trifluoromethyl-thio(seleno)cyanation of alkenes

Maheshwara Reddy Nadiveedhi et al.

GREEN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Three component hydroxyletherification and hydroxylazidation of (trifluoromethyl)alkenes: access to α-trifluoromethyl β-heteroatom substituted tertiary alcohols

Hao Zeng et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Multidisciplinary

Transition-Metal-Mediated and -Catalyzed C-F Bond Activation by Fluorine Elimination

Takeshi Fujita et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Recent Advances in the Intermolecular Oxidative Difunctionalization of Alkenes

Jie Lin et al.

CHEMICAL RECORD (2019)

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Article Chemistry, Organic

Asymmetric Synthesis of Vicinally Bis(trifluoromethyl)-Substituted 3,3-Pyrrolidinyl Spirooxindoles via Organocatalytic 1,3-Dipolar Cycloaddition Reactions

Wen-Run Zhu et al.

SYNTHESIS-STUTTGART (2019)

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Article Chemistry, Applied

Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes

Hyunseok Oh et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Photocatalytic hydroacylation of trifluoromethyl alkenes

Pei Fan et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

A facile method for hydroxytrifluoromethylation of alkenes with Langlois reagent and DMSO

Wei-Guo Shen et al.

GREEN CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

Recent advances in the synthesis and applications of α-(trifluoromethyl)styrenes in organic synthesis

Feitao Tian et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Organic

Manganese-Dioxide-Catalyzed Trifluoromethylation and Azidation of Styrenyl Olefins via Radical Intermediates

Prabhakar Panday et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Applied

Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C-F Bond Cleavage

Liu-Hai Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Organic

Organocatalytic Asymmetric [3+2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines with β-Trifluoromethyl Electron Deficient Alkenes: Access to Vicinally Bis(trifluoromethyl)-Substituted 3,2′-Pyrrolidinyl Spirooxindoles

Yong You et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Multidisciplinary

Catalyst-Free Oxytrifluoromethylation of Alkenes through Paired Electrolysis in Organic-Aqueous Media

Wolfgang Jud et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Organic

Hydroxytrifluoromethylation of Alkenes Using Fluoroform-Derived CuCF3

Xinkan Yang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Recent advances in the synthesis and C-F functionalization of gem-difluoroalkenes

Xuxue Zhang et al.

TETRAHEDRON LETTERS (2017)

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Article Chemistry, Multidisciplinary

Iron-Mediated Chlorotrifluoromethylation of Alkenes with Sodium Trifluoromethanesulfinate

Bin Yang et al.

CHINESE JOURNAL OF CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates

Jieru Yang et al.

CHEMICAL COMMUNICATIONS (2016)

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Article Chemistry, Organic

Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrene Derivatives Using CF3SO2Na as the Trifluoromethyl Source

Yi Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Chemistry, Organic

NMP and O2 as Radical Initiator: Trifluoromethylation of Alkenes to Tertiary β-Trifluoromethyl Alcohols at Room Temperature

Chao Liu et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Organic

Copper-Mediated Radical 1,2-Bis(trifluoromethylation) of Alkenes with Sodium Trifluoromethanesulfinate

Bin Yang et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

Diastereoselective Synthesis of Vicinally Bis(trifluoromethylated) Alkylboron Compounds through Successive Insertions of 2,2,2-Trifluorodiazoethane

Gary A. Molander et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Organic

AgF-Mediated Fluorinative Homocoupling of gem-Difluoroalkenes

Bing Gao et al.

ORGANIC LETTERS (2014)

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Article Chemistry, Multidisciplinary

Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones

Arghya Deb et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Three-Component Oxytrifluoromethylation of Alkenes with Sodium Trifluoromethanesulfinate and Hydroxamic Acid

Xin-Yi Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Article Chemistry, Multidisciplinary

Taming Hot CF3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics

Igor V. Kuvychko et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF3SO2Na: facile access to α,β-bistrifluoromethyl tertiary alcohols

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