4.8 Article

Hydrogen-Atom Transfer Catalysis for C-H Alkylation of Benzylic Fluorides

Related references

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

Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis

Liang Chang et al.

Summary: This review comprehensively summarizes the recent progress in alkoxy radical-mediated transformations under visible light irradiation. The mechanisms of alkoxy radical generation and their impact on synthetic utilizations are discussed. The catalytic generation of alkoxy radicals from abundant alcohols is still in the early stage, but holds great potential.

CHEMICAL REVIEWS (2022)

Review Chemistry, Multidisciplinary

Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis

Kitae Kwon et al.

Summary: This review is a guide for chemists engaged in target-oriented synthesis, summarizing the recent methods and applications of generating nitrogen-centered radicals through photocatalysis. The mild conditions of this approach enable its wide applications in synthesizing various small molecules, highlighting its tremendous utility.

CHEMICAL REVIEWS (2022)

Article Chemistry, Physical

Hydrogen-Atom-Transfer-Mediated Acceptorless Dehydrogenative Cross-Coupling Enabled by Multiple Catalytic Functions of Zwitterionic Triazolium Amidate

Kodai Minami et al.

Summary: An unconventional cooperative catalysis for hydrogen-atom-transfer-mediated acceptorless dehydrogenative cross-coupling is described in this study. By using specific catalysts, C-H/C-H cross-couplings between heteroatom-containing C-H donors and enamides or 1,1-diarylethenes were achieved under visible-light irradiation without the need for oxidants, hydrogen evolution catalysts, or electrodes. The key to this catalysis is the susceptibility of the conjugate acid of the triazolium amidate, amide triazolium, to single-electron reduction to complete the catalytic cycle.

ACS CATALYSIS (2022)

Article Chemistry, Organic

Site-Selective Late-Stage C-H Functionalization via Thianthrenium Salts

Florian Berger et al.

Summary: C-H functionalization is an efficient method to increase the complexity of organic molecules rapidly, but improving selectivity remains a challenge. By utilizing sulfonium salts, we have developed a highly selective approach for aromatic C-H functionalization, enhancing not only the efficiency of the reaction but also expanding the scope of follow-up reactions.

SYNLETT (2022)

Review Chemistry, Multidisciplinary

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration

Luca Capaldo et al.

Summary: Direct photocatalyzed hydrogen atom transfer (d-HAT) is a preferred method for the synthesis of aliphatic C-H bonds in organic compounds. Selective C-H bond elaboration can be achieved by choosing suitable hydrogen abstractors and reaction additives. This review provides a comprehensive survey of the synthetic applications of photocatalyzed d-HAT.

CHEMICAL REVIEWS (2022)

Review Chemistry, Multidisciplinary

Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Rolando Cannalire et al.

Summary: Late stage functionalization is a powerful tool for accelerating the identification of structure-activity relationships and optimizing ADME profiles of drugs. Visible-light photocatalysis offers a smooth and clean functionalization approach for drugs, with a critical assessment of current literature and highlighting expected future progress and potential applications in the field.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides

Xin Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Applied

Free-Radical-Promoted Alkenylation of C(sp3)-H Bond in Chloroalkane with Cinnamic Acid and β-Nitrostyrene

Minzhi Sun et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Multiple Catalytic C-H Bond Functionalization for Natural Product Synthesis

Olivier Baudoin

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

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

Luca Capaldo et al.

GREEN CHEMISTRY (2020)

Article Chemistry, Organic

9-Borabicyclo[3.3.l]nonane-induced Friedel-Crafts benzylation of arenes with benzyl fluorides

Jing Guo et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Eosin Y as a Direct Hydrogen-Atom Transfer Photocatalyst for the Functionalization of C-H Bonds

Xuan-Zi Fan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Activation of C-F bonds alpha to C-C multiple bonds

Jean-Denys Hamel et al.

CHEMICAL COMMUNICATIONS (2018)

Article Multidisciplinary Sciences

Defluorosilylation of fluoroarenes and fluoroalkanes

Benqiang Cui et al.

NATURE COMMUNICATIONS (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)

Review Chemistry, Multidisciplinary

Decatungstate Anion for Photocatalyzed Window Ledge Reactions

Davide Ravelli et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Multidisciplinary

C-C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation

Jiangtao Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

Tim Cernak et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Organic

Photoredox Catalysis in Organic Chemistry

Megan H. Shaw et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Multidisciplinary Sciences

Catalytic alkylation of remote C-H bonds enabled by proton-coupled electron transfer

Gilbert J. Choi et al.

NATURE (2016)

Article Chemistry, Organic

Cascade Arylalkylation of Activated Alkenes: Synthesis of Chloro- and Cyano-Containing Oxindoles

Xueqin Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Photochemically induced radical reactions with furanones

Michael Oelgemoeller et al.

PURE AND APPLIED CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Characterizing chain processes in visible light photoredox catalysis

Megan A. Cismesia et al.

CHEMICAL SCIENCE (2015)

Article Chemistry, Multidisciplinary

Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding

Pier Alexandre Champagne et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Review Chemistry, Multidisciplinary

Photoorganocatalysis. What for?

Davide Ravelli et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Organic

Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding

Pier Alexandre Champagne et al.

ORGANIC LETTERS (2013)

Article Chemistry, Organic

Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides

George Blessley et al.

ORGANIC LETTERS (2012)

Review Chemistry, Multidisciplinary

Decatungstate as an efficient photocatalyst in organic chemistry

Manolis D. Tzirakis et al.

CHEMICAL SOCIETY REVIEWS (2009)

Article Chemistry, Multidisciplinary

Hydrogen bonding and catalysis of solovlysis of 4-methoxybenzyl fluoride

MM Toteva et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)