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Literature DB >> 31057188

Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Arghya Banerjee¹, Zhen Lei¹, Ming-Yu Ngai^1,2.

Abstract

Visible light photoredox catalysis has enabled easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-ketoacids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes such recent progress of visible-light-driven acyl radical generation using transition metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts.

Entities: CellLine Chemical Disease Gene Species

Keywords: Acyl Radical; Acylation; Cross-Coupling; Oxidation; Photoredox Catalysis; Reduction; Single Electron Transfer; Visible-Light

Year: 2018 PMID： 31057188 PMCID： PMC6497162 DOI： 10.1055/s-0037-1610329

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

72 in total

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Authors: Chryssostomos Chatgilialoglu; David Crich; Mitsuo Komatsu; Ilhyong Ryu
Journal: Chem Rev Date: 1999-08-11 Impact factor: 60.622

2. Determination of the C4-H bond dissociation energies of NADH models and their radical cations in acetonitrile.

Authors: Xiao-Qing Zhu; Hai-Rong Li; Qian Li; Teng Ai; Jin-Yong Lu; Yuan Yang; Jin-Pei Cheng
Journal: Chemistry Date: 2003-02-17 Impact factor: 5.236

3. Gas-Phase and Solution-Phase Homolytic Bond Dissociation Energies of H-N(+) Bonds in the Conjugate Acids of Nitrogen Bases.

Authors: Wei-Zhong Liu; Frederick G. Bordwell
Journal: J Org Chem Date: 1996-07-12 Impact factor: 4.354

Review 4. Organocatalysis by N-heterocyclic carbenes.

Authors: Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal: Chem Rev Date: 2007-10-23 Impact factor: 60.622

5. Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions.

Authors: Luisa Benati; Gianluca Calestani; Rino Leardini; Matteo Minozzi; Daniele Nanni; Piero Spagnolo; Samantha Strazzari
Journal: Org Lett Date: 2003-04-17 Impact factor: 6.005

6. Probing the reactivity of photoinitiators for free radical polymerization: time-resolved infrared spectroscopic study of benzoyl radicals.

Authors: Christopher S Colley; David C Grills; Nicholas A Besley; Steffen Jockusch; Pavel Matousek; Anthony W Parker; Michael Towrie; Nicholas J Turro; Peter M W Gill; Michael W George
Journal: J Am Chem Soc Date: 2002-12-18 Impact factor: 15.419

Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

1. Chemistry of Acyl Radicals.

2. Determination of the C4-H bond dissociation energies of NADH models and their radical cations in acetonitrile.

3. Gas-Phase and Solution-Phase Homolytic Bond Dissociation Energies of H-N(+) Bonds in the Conjugate Acids of Nitrogen Bases.

Review 4. Organocatalysis by N-heterocyclic carbenes.

5. Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions.

6. Probing the reactivity of photoinitiators for free radical polymerization: time-resolved infrared spectroscopic study of benzoyl radicals.

7. Low-temperature ag/pd-catalyzed decarboxylative cross-coupling of aryl triflates with aromatic carboxylate salts.

8. Mechanism of base activation of persulfate.

9. Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates.

10. Synthesis of ketones from alpha-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling.

1. High-throughput photocapture approach for reaction discovery.

2. β-Selective Aroylation of Activated Alkenes by Photoredox Catalysis.

3. Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation.

4. Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

5. Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Review 6. Photoredox-Catalyzed C-H Functionalization Reactions.

7. Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis.

Review 8. Pd(II)-Catalyzed C-H Acylation of (Hetero)arenes-Recent Advances.

9. Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

10. Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.