4.7 Article

Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones

Related references

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

Single-Electron Transfer Reactions Enabled by N-Heterocyclic Carbene Organocatalysis

Qing-Zhu Li et al.

Summary: In recent years, the N-heterocyclic carbene (NHC) organocatalysis field has seen the emergence of long-awaited single-electron transfer (SET) reactions, providing opportunities to develop new catalytic modes and useful synthetic methods.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions**

Ludivine Delfau et al.

Summary: This study reported the synthesis of acyl azolium salts from various types of carbenes and the generation of their corresponding radicals and enolates, revealing the role of additives in the redox behavior of these compounds and correcting misconceptions about radical transformations of aldehyde derivatives. The reducing ability of enolates derived from certain carbenes was found to be underestimated, and catalytic intermediates were shown to transfer electrons efficiently at room temperature. Enol derivatives of certain carbenes were identified as powerful reducing agents.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Zhijun Zuo et al.

Summary: This study presents a cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis. The key step involves a radical/radical cross coupling, leading to metal-free reaction conditions and a wide range of functional group tolerances.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay

Yu Gao et al.

Summary: The study presents an unprecedented regioselective, intermolecular 1,2-cyanoalkylacylation of feedstock alkenes using N-heterocyclic carbene (NHC) organocatalysis. The exquisite control over the radical relay process by the NHC organocatalyst enables a general platform for the synthesis of valuable ketonitriles under mild, transition-metal-free conditions. This protocol highlights the potential for late-stage functionalization of pharmaceutical architectures and natural products.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

N-Heterocyclic Carbene/Magnesium Cocatalyzed Radical Relay Assembly of Aliphatic Keto Nitriles

Lei Chen et al.

Summary: A novel method for three-component acylcyanoalkylation of alkenes with cycloketone oxime esters and aldehydes under mild reaction conditions was developed, offering access to diverse multifunctionalized aliphatic keto nitrile structures. This strategy is suggested to proceed through a radical relay mechanism involving a single electron transfer event of a Mg/matched Breslow intermediate/oxime ester electron-donating acceptor (EDA) complex.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

C-C Bond Acylation of Oxime Ethers via NHC Catalysis

Hai-Bin Yang et al.

Summary: A novel N-heterocyclic carbene (NHC)-catalyzed strategy has been developed to efficiently activate C-C bonds without using toxic transitional metals, resulting in the synthesis of ketonitrile as a useful building block for nitrogen-containing pharmacophores.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Norrish type II reactions of acyl azolium salts

Andreas Mavroskoufis et al.

Summary: The photochemical reactivity of acyl azolium salts derived from aliphatic carboxylic acids was investigated, showing Norris type II elimination reactions and Norris-Yang cyclization under UVA light irradiation. These results demonstrate the influence of NHCs on the absorption properties and photochemical reactivity of carbonyl groups during a catalytic cycle.

TETRAHEDRON (2021)

Article Chemistry, Physical

Carbene-Catalyzed Alkylation of Carboxylic Esters via Direct Photoexcitation of Acyl Azolium Intermediates

Shi-Chao Ren et al.

Summary: A carbene-catalyzed reductive coupling reaction of carboxylic esters and substituted Hantzsch esters has been disclosed, which is promoted by visible light irradiation and allows for incorporation of sophisticated structures, including those found in medicines, into ketone molecules under mild conditions.

ACS CATALYSIS (2021)

Article Chemistry, Physical

Light-Driven N-Heterocyclic Carbene Catalysis Using Alkylborates

Yukiya Sato et al.

Summary: This research developed a new method for radical-radical coupling, utilizing light-driven NHC organocatalysis to achieve this reaction, and generating alkyl radicals through borates for single electron transfer. This protocol enables cross-coupling between alkylborates and acyl imidazoles, as well as radical relay-type alkylacylations of alkenes with alkylborates and acyl imidazoles.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

Kun Liu et al.

Summary: N-Heterocyclic carbene (NHC) catalysis is a versatile tool in modern synthetic chemistry, often used in concert with a second catalytic moiety to expand reaction scope. Triple catalysis, merging three different catalytic modes in a single process, has been recently studied, allowing for the synthesis of complex compounds. In a reported study, alpha-C-H acylation of alkenes using NHC, sulfinate, and photoredox cooperative triple catalysis was achieved, highlighting the potential of such synergistic catalytic systems.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Organic

Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis

David Kieslich et al.

Summary: The nucleophilic addition of a cyanide anion to a carbonyl group serves as the basis for several cyanide-catalyzed organic reactions, with examples including the benzoin condensation and the Michael-Stetter reaction. Apart from the fundamental reactions, variants like the silyl-benzoin coupling and cyanide-catalyzed heterocyclic syntheses are also covered.

SYNTHESIS-STUTTGART (2021)

Article Multidisciplinary Sciences

Benzylic C-H acylation by cooperative NHC and photoredox catalysis

Qing-Yuan Meng et al.

Summary: Methods enabling site-selective acylation of sp3 C-H bonds in complex organic molecules are not well explored. Here, the authors present a direct and site-selective acylation of benzylic C-H bonds through the combination of N-heterocyclic carbene (NHC) and photoredox catalysis, offering options for preparing benzyl aryl ketones.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Anna Bay et al.

Summary: This study reports the light-driven synthesis of aliphatic and alpha-amino ketones using single-electron NHC operators. Computational and experimental results show that the reactivity of the key radical intermediate depends on the substrate and can be modulated through steric and electronic parameters of the NHC. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Radical Relay Trichloromethylacylation of Alkenes through N-Heterocyclic Carbene Catalysis

Mayu Kusakabe et al.

Summary: The vicinal trichloromethylacylation of alkenes using tetrachloromethane and aldehydes has been achieved through N-heterocyclic carbene catalysis. The reaction involves single electron transfer to generate persistent Breslow intermediate-derived ketyl radical and a transient trichloromethyl radical before forming the atom transfer radical addition product.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

Joshua L. Zhu et al.

Summary: Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Inspired by strategies using dual N-heterocyclic carbene catalysis and photocatalysis, dimethylimidazolium esters were prepared as alkoxycarbonyl radical surrogates under photocatalytic conditions, showing synthetic utility in coupling with an oxidatively generated alkyl radical to form esters.

TETRAHEDRON (2021)

Article Multidisciplinary Sciences

Aryl radical-mediated N-heterocyclic carbene catalysis

Yuki Matsuki et al.

Summary: This article discusses the successful application of NHC-catalyzed aryl radical reactions in various arylations. The method allows for the generation of aryl radicals from halides through single electron transfer processes, providing a metal-free approach for radical reactions.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Physical

Dual Catalysis Relay: Coupling of Aldehydes and Alkenes Enabled by Visible-Light and NHC-Catalyzed Cross-Double C-H Functionalizations

Ming-Shang Liu et al.

Summary: This translation describes a method of intermolecular vinylation of aldehydes using alkenes as the vinylating reagents through sequential two-fold C-H functionalizations and a dual catalysis relay enabled cross-dehydrogenative coupling mechanism.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Recent advances in the chemistry and applications of N-heterocyclic carbenes

Peter Bellotti et al.

Summary: N-Heterocyclic carbenes have attracted significant interest due to their versatility, modularity and strong coordinating properties, leading to a rapid increase in utilization across various fields in the past decade. Future directions and recent developments in the field are also highlighted in this review.

NATURE REVIEWS CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now

Monika Pareek et al.

Summary: N-Heterocyclic carbenes (NHCs) are popular organocatalysts known for their umpolung reactivity on aldehydes and ketones. Recent research has focused on gaining insights into the formation and characterization of Breslow intermediates, which play a central role in organocatalytic reactions.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

The Persistent Radical Effect in Organic Synthesis

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides

Andreas Mavroskoufis et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

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

Anna V. Bay et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Multidisciplinary Sciences

High-throughput photocapture approach for reaction discovery

Alison A. Bayly et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2020)

Article Chemistry, Multidisciplinary

Cooperative NHC and Photoredox Catalysis for the Synthesis of β-Trifluoromethylated Alkyl Aryl Ketones

Qing-Yuan Meng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Physical

Light-Promoted Organocatalysis with N-Heterocyclic Carbenes

Andreas Mavroskoufis et al.

CHEMPHOTOCHEM (2020)

Article Chemistry, Physical

N-Heterocyclic Carbene-Based Catalysis Enabling Cross-Coupling Reactions

Hirohisa Ohmiya

ACS CATALYSIS (2020)

Review Chemistry, Organic

Recent Advances in Stetter Reaction and Related Chemistry: An update

Majid M. Heravi et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Light opens a new window for N-heterocyclic carbene catalysis

Jing Liu et al.

CHEMICAL SCIENCE (2020)

Review Chemistry, Multidisciplinary

Recent advances in N-heterocyclic carbene-based radical catalysis

Takuya Ishii et al.

CHEMICAL SCIENCE (2020)

Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

Takuya Ishii et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes

Takuya Ishii et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates

Matthieu Jouffroy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Photoredox Catalysis for the Generation of Carbon Centered Radicals

Jean-Philippe Goddard et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Multidisciplinary

Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds

Vincent Corce et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Organic

Organotrifluoroborates: Another Branch of the Mighty Oak

Gary A. Molander

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β-Hydroxylation of Enals

Yuexia Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers

Idris Karakaya et al.

ORGANIC LETTERS (2015)

Review Multidisciplinary Sciences

An overview of N-heterocyclic carbenes

Matthew N. Hopkinson et al.

NATURE (2014)

Article Chemistry, Multidisciplinary

The Mukaiyama Aldol Reaction: 40Years of Continuous Development

Jun-ichi Matsuo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Visible-light-induced hydroalkoxymethylation of electron-deficient alkenes by photoredox catalysis

Kazuki Miyazawa et al.

CHEMICAL COMMUNICATIONS (2013)

Article Chemistry, Applied

Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis

Yusuke Yasu et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

Review Chemistry, Multidisciplinary

Organocatalytic umpolung: N-heterocyclic carbenes and beyond

Xavier Bugaut et al.

CHEMICAL SOCIETY REVIEWS (2012)

Biographical-Item Chemistry, Organic

Discovery of the Michael Reaction IN MEMORIAM

Takashi Tokoroyama

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

Review Chemistry, Multidisciplinary

Organotrifluoroborates: Protected boronic acids that expand the versatility of the Suzuki coupling reaction

Gary A. Molander et al.

ACCOUNTS OF CHEMICAL RESEARCH (2007)

Review Chemistry, Organic

Synthesis of dihydrofurans substituted in the 2-position

TG Kilroy et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2005)

Review Chemistry, Multidisciplinary

Strategy and methodology development for the total synthesis of polyether ionophore antibiotics

MM Faul et al.

CHEMICAL REVIEWS (2000)