4.7 Article

Photoinduced C-H monofluoroalkenylation with gem-difluoroalkenes through hydrogen atom transfer under batch and flow conditions

Related references

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

Advances in the E → Z Isomerization of Alkenes Using Small Molecule Photocatalysts

Tomas Nevesely et al.

Summary: Geometrical E → Z alkene isomerization, a critical topic in organic photochemistry, has seen significant advancements in recent years. By utilizing energy transfer catalysis, directed isomerization of alkenes can be achieved. This review summarizes the progress in the field of geometric alkene isomerization enabled by energy transfer catalysis from 2000 to 2020, and discusses the reaction mechanisms, induction models, and applications in total synthesis and regioselective reactions.

CHEMICAL REVIEWS (2022)

Article Chemistry, Physical

Photocatalytic (Het)arylation of C(sp3)-H Bonds with Carbon Nitride

Saikat Das et al.

Summary: Graphitic carbon nitride materials have shown potential in synthetic photocatalysis for direct arylation of C(sp(3))-H bonds, with a broad synthetic scope and high selectivity. The unique energy-transfer process (EnT) from the organic semiconductor to the nickel complex enables diverse applications, including late-stage functionalization of drugs.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Site-Selective Defluorinative sp3 C-H Alkylation of Secondary Amides

Wen-Jun Yue et al.

Summary: This new method features mild conditions, wide applicability, and exquisite site-selectivity, allowing for the rapid and reliable incorporation of gemdifluoroalkene motifs into previously unfunctionalized sp(3) sites, thus providing a new platform for introducing carbonyl isosteres at saturated hydrocarbon sites.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis

Leitao Huan et al.

Summary: The study presents an asymmetric benzylic C-H acylation reaction using nickel and photoredox dual catalysis, with carboxylic acids as acyl surrogates, to synthesize high enantioselective alpha-aryl ketones. This method can convert various feedstock carboxylic acids and simple alkylarenes into valuable alpha-aryl ketones, showcasing potential applications in gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest that a bromine-radical-mediated C-H activation strategy plays a crucial role in this reaction.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Physical

Stereo- and Enantioselective Benzylic C-H Alkenylation via Photoredox/Nickel Dual Catalysis

Xiaokai Cheng et al.

Summary: A stereo- and enantioselective benzylic C-H alkenylation via photoredox/nickel catalysis has been developed, allowing for smooth cross-coupling reactions of readily available alkylbenzenes and alkenyl bromides, even with complicated molecules. The reaction conditions are mild with good functional group tolerance, yielding chiral allylic compounds with high ee and E/Z ratio. Additionally, a triplet-energy-transfer-inhibiting strategy has been developed for stereoselective synthesis of alkenes under visible-light photocatalysis, with the coordination pattern of nickel with chiral bis-imidazoline ligand elucidated based on experiments and X-ray diffraction.

ACS CATALYSIS (2021)

Review Chemistry, Organic

Photocatalytic C-F Bond Activation of Fluoroarenes, gem-Difluoroalkenes and Trifluoromethylarenes

Wengang Xu et al.

Summary: The recent development of photocatalytic C-F bond activation of fluorinated compounds, including fluoroarenes, gem-difluoroalkenes, and trifluoromethylarenes, has provided an efficient way to synthesize novel fluorinated products and degrade stable fluorinated pollutants. The light-induced direct C-F bond activation under mild conditions for the production of various functionalities is considered one of the most advanced and efficient methodologies in organic transformations.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Physical

Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis

Hui Cao et al.

Summary: HAT technology provides a simple method to generate open-shell radical intermediates from R-H bonds, while photoinduced intermolecular HAT reactions have seen significant developments in efficiency, selectivity, and versatility, offering new opportunities for green synthesis.

CHEM CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Visible-Light-Induced Selective Defluoroborylation of Polyfluoroarenes, gem-Difluoroalkenes, and Trifluoromethylalkenes

Wengang Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Dehydrogenative Coupling of Benzylic and Aldehydic C-H Bonds

Tairin Kawasaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Physical

Bromide-Promoted Visible-Light-Induced Reductive Minisci Reaction with Aldehydes

Zhongzhen Wang et al.

ACS CATALYSIS (2020)

Article Chemistry, Applied

C(sp3)-C(sp3) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis

Marilia S. Santos et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Pushing the boundaries of C-H bond functionalization chemistry using flow technology

Sebastian Govaerts et al.

JOURNAL OF FLOW CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Recent Advances in Transition Metal-catalyzed Functionalization of gem-Difluoroalkenes

Suvajit Koley et al.

ISRAEL JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Photoinduced Specific Acylation of Phenolic Hydroxy Groups with Aldehydes

Tairin Kawasaki et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Direct Enantioselective C(sp3)-H Acylation for the Synthesis of α-Amino Ketones

Xiaomin Shu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?

Luca Capaldo et al.

GREEN CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

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

Takeshi Fujita et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Nucleophilic Substitution of gem-Difluoroalkenes with TMSNu Promoted by Catalytic Amounts of Cs2CO3

Ling-Feng Jiang et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Multidisciplinary Sciences

Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysis

Xiaokai Cheng et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Organic

Metal-Free Access to (E/Z)-α-Fluorovinyl Phosphorus Compounds from gem-Difluorostyrenes

Yingyuan Peng et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Direct Cross-Coupling of Allylic C(sp(3))-H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis

Long Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Organic

Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes

Liting Yu et al.

ORGANIC LETTERS (2018)

Review Chemistry, Organic

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Luca Capaldo et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

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

Xuxue Zhang et al.

TETRAHEDRON LETTERS (2017)

Article Chemistry, Multidisciplinary

A Personal Perspective on the Future of Flow Photochemistry

Timothy Noel

JOURNAL OF FLOW CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Rhodium(III)-catalyzed regio- and stereoselective benzylic α-fluoroalkenylation with gem-difluorostyrenes

Lingheng Kong et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Visible light photocatalytic decarboxylative monofluoroalkenylation of α-amino acids with gem-difluoroalkenes

Jingjing Li et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Functionalization of C-H Bonds by Photoredox Catalysis

Qixue Qin et al.

CHEMICAL RECORD (2017)

Article Chemistry, Multidisciplinary

Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage

Sai-Hu Cai et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Two-Fold Unsymmetrical C(sp3)-H Functionalization and Double C-F Substitution

Linyong Li et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling

Jin Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations

Drew R. Heitz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Multidisciplinary Sciences

Rhodium-catalysed C(sp2)-C(sp2) bond formation via C-H/C-F activation

Panpan Tian et al.

NATURE COMMUNICATIONS (2015)

Article Chemistry, Organic

Iron-catalyzed N-alkylation using π-activated ethers as electrophiles

Xiaohui Fan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

Article Chemistry, Organic

Iron-Catalyzed Ring-Opening Azidation and Allylation of O-Heterocycles

Yoshinari Sawama et al.

ORGANIC LETTERS (2013)

Review Chemistry, Multidisciplinary

Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems

Giorgio Chelucci

CHEMICAL REVIEWS (2012)

Review Chemistry, Multidisciplinary

Deciding Whether To Go with the Flow: Evaluating the Merits of Flow Reactors for Synthesis

Ryan L. Hartman et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Physical

Estimation of Standard Reduction Potentials of Halogen Atoms and Alkyl Halides

Abdirisak A. Isse et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2011)

Review Chemistry, Multidisciplinary

C-F Bond Activation in Organic Synthesis

Hideki Amii et al.

CHEMICAL REVIEWS (2009)

Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)