Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

Article Chemistry, Multidisciplinary

Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer

Joshua L. Zhu et al.

Summary: Stable acyl azolium salts can undergo intermolecular HAT reaction upon LED irradiation to afford ketones.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

DBU-Mediated Isomerization/6-π Electro-Cyclization/Oxidation Cascade of Sulfonyl-Substituted Allenyl Ketones for the Construction of Hetero-1,3,5-Trisubstituted Benzene

Lihong Wang et al.

Summary: 1,3,5-tri-substituted benzene rings with unique properties have diverse applications in materials, driving the rapid development of their synthesis. Despite the importance, direct construction of hetero-1,3,5-trisubstituted benzene core remains underdeveloped. Here, we achieved a DBU-mediated isomerization/6-pi electro-cyclization/oxidative aromatization cascade of sulfonyl-substituted allenyl ketones under air atmosphere (DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). This versatile protocol, featuring metal-free conditions, easy operation, and broad functional group tolerance, provides a new avenue for constructing hetero-1,3,5-tri-substituted benzene.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photochemical Organocatalytic Benzylation of Allylic C-H Bonds

Emilien Le Saux et al.

Summary: We report a radical-based organocatalytic method for the direct benzylation of allylic C-H bonds. This method uses nonfunctionalized allylic substrates and readily available benzyl radical precursors, and is driven by visible light. By controlling two orthogonal radical generation paths, it enables the selective coupling of allylic and benzylic radicals, thus expanding the synthetic potential of organic chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Driven Bisfunctionalization of Unactivated Olefins via the Merger of Proton-Coupled Electron Transfer and Carbene Catalysis

Bei Zhang et al.

Summary: In this study, a novel NHC and photo-co-catalyzed alkylacylation of olefins using diazo esters as radical source is reported, presenting a new idea for transient radical generation with the only byproduct being N-2. Compared to previous methods, this process shows great atom economy with reduced discard fragments.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

N-heterocyclic carbene-catalyzed arene formation reactions

Tingting Li et al.

Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.

SCIENCE CHINA-CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones

Lihong Wang et al.

Summary: The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C-C bonds was achieved using N-Heterocyclic carbene (NHC) catalyzed radical transformations. This method successfully realized highly selective cross-coupling between acyl radicals and alkyl radicals for efficient construction of C-C bonds. The study further investigated the cross-coupling reaction of acyl radicals with vinyl radicals, providing valuable insights into the mechanism.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis

Hua Huang et al.

Summary: In this study, an NHC/photoredox dual catalytic cross-coupling of alkyl trifluoroborates with acid fluorides was developed. This method offers a novel solution for the classical acylative Suzuki coupling chemistry, allowing for the rapid synthesis of various ketones under mild conditions.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Physical

N-Heterocyclic Carbene-Photocatalyzed Tricomponent Regioselective 1,2-Diacylation of Alkenes Illuminates the Mechanistic Details of the Electron Donor-Acceptor Complex-Mediated Radical Relay Processes

Shengfei Jin et al.

Summary: Progress in developing photocatalytic reactions requires a detailed understanding of the underlying mechanisms, especially those involving electron donor-acceptor complexes. This study reports a new method for regioselective installation of two different acyl groups through photocatalytic alkene 1,2-diacylation. The research highlights the central role of electron donor-acceptor complexes in mediating the photoinduced charge transfer process and sheds light on the catalytic activities of N-heterocyclic carbenes in radical reactions.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Physical

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

Xiaochen Wang et al.

Summary: We report a mild and operationally simple method for the direct acylation of α-amino C(sp(3))-H bonds from carboxylic acids. The method combines carbene and photoredox catalysis and successfully synthesizes structurally diverse α-amino ketones through the cross-coupling reactions between a wide range of carboxylic acids and readily available N-alkyl anilines. This method demonstrates a broad substrate scope and compatibility with various functional groups.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Organic

Radical Acylalkylation of 1,3-Enynes To Access Allenic Ketones via N-Heterocyclic Carbene Organocatalysis

Yan-Qing Liu et al.

Summary: An N-heterocyclic carbene organocatalytic 1,4-difunctionalization of 1,3-enynes has been developed, allowing efficient synthesis of allenic ketones bearing diverse substituents. Preliminary mechanistic studies suggest a radical reaction pathway for this organocatalytic acylalkylation process.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans

Xiaoye Yu et al.

Summary: In this study, a method using aroyl fluorides as bifunctional reagents for the dearomatization of dihydrobenzofurans was reported. The reaction proceeds through cooperative NHC/photoredox catalysis, resulting in the formation of 2,3-difunctionalized dihydrobenzofuran compounds with moderate to high yield and high diastereoselectivity. The reaction also exhibits broad substrate scope and high functional group compatibility.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation

Anna Bay et al.

Summary: This study presents a novel tandem carbene and photoredox-catalyzed process for the synthesis of substituted cycloalkanones, offering a new approach for constructing important cyclic scaffolds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones

Shi-Chao Ren et al.

Summary: This study reports a decarboxylative radical coupling of carboxylic acids and acyl imidazoles catalyzed by an N-heterocyclic carbene and photocatalyst. The carboxylic acids serve as direct radical precursors, and suitable acyl imidazoles can also be generated in situby a reaction with CDI. The method is extended to three-component coupling by using alkenes as a third coupling partner via a radical relay process. The mild reaction conditions, simplicity, and use of easily available starting materials make this method a powerful strategy for constructing complex ketones and modifying natural products and medicines.

NATURE COMMUNICATIONS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diastereoselective Radical Aminoacylation of Olefins through N-Heterocyclic Carbene Catalysis

Wen-Deng Liu et al.

Summary: Significant advancements have been made in radical-mediated reactions through covalent-based organocatalysis. This study demonstrates the generation of iminyl and amidyl radicals via tive aminoacylation of trisubstituted alkenes, providing a straightforward access to a variety of heterocycles with vicinal stereocenters.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Borylative Amidation of Allenes

Seunghwan Byun et al.

Summary: This study reveals an approach for the copper-catalyzed synthesis of enantioenriched amides bearing an alpha-stereogenic center. The addition of an allyl copper species to an isocyanate allows access to alpha-substituted chiral amides in high yields and high-to-excellent enantioselectivities. The utility of alpha-vinyl beta-boryl amides in synthesis is highlighted by the diversification of products to afford highly useful scaffolds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Applied

Cooperative NHC/Photoredox Catalysis: Three Component Radical Coupling of Aroyl Fluorides, Styrenes and Alcohols

Nadine Doeben et al.

Summary: Cooperative NHC/photoredox catalysis is an important research field. Tertiary alcohols are used as alkyl radical precursors to perform three component radical coupling, leading to the synthesis of alpha-arylated alkyl aryl ketones. The reaction involves the formation of an acyl azolium ion from an aroyl fluoride with the NHC catalyst, which is then reduced by the photoredox catalyst to generate a ketyl radical anion. The generated C-radicals derived from the alcohol add to the styrene derivative and undergo cross coupling with the ketyl radical, resulting in the targeted ketone after NHC fragmentation.

ADVANCED SYNTHESIS & CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Organic

Synthesis of ?-Thiolated-?-arylated Ketones Enabled by Photoredox and N-Heterocyclic Carbene-Catalyzed Radical Relay of Alkenes with Disulfides and Aldehydes

Hai-Wu Du et al.

Summary: A straightforward method to access beta-thiolated ketones from aldehydes, alkenes, and disulfides using the combination of photocatalysis and N-heterocyclic carbene catalysis is reported. The sequential radical addition to alkenes and subsequent radical-radical coupling cascade process simultaneously forge C-S and C-C bonds. The method exhibits a broad functional group tolerance.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Physical

Organic Photoredox-Catalyzed Silyl Radical Generation from Silylboronate

Naho Takemura et al.

Summary: This article presents a visible-light-driven method for silyl radical generation, which is further enhanced by recent advancements in silylboronate synthesis.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Organic

CF2Br2 as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis

Lei Chen et al.

Summary: In this study, commercially available CF2Br2 has been utilized as a convenient source for incorporating the gem-difluorovinyl motif into 1,3-enynes through an N-heterocyclic carbene catalyzed reaction. The reaction proceeds through a cascade three-component radical relay/elimination process. This methodology offers mild conditions, easily accessible starting materials, wide substrate scope, and easy late-stage functionalization, providing an alternative strategy for constructing a new class of functionalized gem-difluorovinyl allenes.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible light-mediated NHCs and photoredox co-catalyzed radical 1,2-dicarbonylation of alkenes for 1,4-diketones

Lihong Wang et al.

Summary: This paper presents a method for the selective 1,2-dicarbonylation of alkenes using NHCs and photocatalysis as co-catalysts, which allows for the construction of structurally diverse 1,4-diketones.

SCIENCE CHINA-CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Physical

Radical NHC Catalysis

Kun Liu et al.

Summary: Radical/radical cross-coupling reactions are efficient and direct methods for constructing chemical bonds. The widespread application of persistent radical effect (PRE) has been limited by the fact that the known types of transient radicals far outnumber the known types of persistent radicals. Recent research has focused on developing efficient cross-coupling reactions between transient radicals, and transition-metal catalysis has been successfully used to prolong radical lifetimes, enabling their utilization in formal radical/radical cross-couplings.

ACS CATALYSIS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

N-heterocyclic carbene-catalyzed radical reactions

Kun-Quan Chen et al.

Summary: In recent years, NHC-catalyzed radical reactions have been gaining attention for their potential to create new activation modes previously inaccessible. Further research and understanding of this emerging area is warranted to explore its synthetic techniques and advantages.

SCIENCE CHINA-CHEMISTRY (2021)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Jose M. Alonso et al.

Summary: The allene functionality, specifically the allenol, has evolved from a chemical curiosity to a common building block in modern organic chemistry, with unique reactivity and frequent occurrence in naturally systems. This Review highlights the significant contributions to the chemistry of allenols in the past decade, focusing on their synthesis, reactivity, and presence in natural products.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Organic

N-Heterocyclic Carbene-Catalyzed 1,4-Alkylacylation of 1,3-Enynes

Yuxing Cai et al.

Summary: This report describes a successful organocatalytic 1,4-alkylacylation of 1,3-enynes using a ketyl radical generated from single-electron oxidation of the Breslow intermediate as a coupling partner of allenyl radicals. The transformation exhibited remarkable tolerance to both aromatic and radical precursors.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

Fu-Dong Lu et al.

Summary: By synergetic photoredox/copper catalysis, enantioselective carbocyanation of 1,3-dienes can be achieved with high efficiency and selectivity, and the method shows good potential for expansion to other substrates such as 1,3-enynes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Physical

1,4-Alkylcarbonylation of 1,3-Enynes to Access Tetra-Substituted Allenyl Ketones via an NHC-Catalyzed Radical Relay

Lei Chen et al.

Summary: In this study, allenyl radicals were successfully generated by N-heterocyclic carbene (NHC) organocatalysis and applied in a three-component radical relay 1,4-alkylcarbonylation reaction without metal participation. This strategy allowed for the convenient synthesis of a range of synthetically challenging tetra-substituted allenyl ketones with high regioselectivity, demonstrating the key role of Csp-C(O)sp(2) radical-radical coupling in constructing the allenyl ketone motifs.

ACS CATALYSIS (2021)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes: An Alternative to Kharasch-Sosnovsky Reaction

Peng-Zi Wang et al.

Summary: A new method for three-component coupling reaction using chiral copper catalyst and purple-LED irradiation as an alternative to allylic oxidation was reported. The reaction features mild conditions, broad scope, and high functional group tolerance, making it useful for late-stage modification of pharmaceuticals and natural products. Detailed mechanistic studies support a radical-based reaction pathway.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

Xue-Qiang Chu et al.

Summary: Sulfonyl-containing compounds and their variants have great reactive flexibility, playing a key role in radical transformations and facilitating the formation of new bond strategies. These compounds have opened up new opportunities in synthetic chemistry with their incredible reactive properties.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling

Jun Chen et al.

Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Diastereo- and Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Lei Wang et al.

Summary: A novel cobalt-catalyzed reaction has been introduced in this article, which efficiently introduces allyl groups into molecules with stereoselective formation of diversified enantioenriched homoallylic alcohols. The mechanism involves allyl radical intermediates and represents a new strategy for enantioselective transformations using chiral Co complexes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Physical

N-Heterocyclic Carbene-Catalyzed Four-Component Reaction: Chemoselective Cradical-Cradical Relay Coupling Involving the Homoenolate Intermediate

Zhen Li et al.

Summary: This study reports an organocatalytic four-component relay radical coupling to access a broad spectrum of beta-tertiary-gamma-quaternary carboxylic acid derivatives, overcoming the synthetic bottleneck of introducing sterically demanding side chains. The high site control achieved using a triazolium N-heterocyclic carbene catalyst and a transient acyl trapping strategy allows for the preparation of diversified carboxylic acid derivatives in a single pot.

ACS CATALYSIS (2021)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals

Martin Berger et al.

Summary: The study presents the first catalytic enantioselective conjugate addition of allyl groups to alpha, beta-unsaturated aldehydes, utilizing the visible-light-excitation of chiral iminium ions to activate allyl silanes toward the formation of allylic radicals. This radical mechanism overcomes issues seen in traditional conjugate allylation processes and selectively installs prenyl fragments at the beta-carbon of enals.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in electrochemical oxidative cross-coupling with hydrogen evolution involving radicals

Yong Yuan et al.

Summary: Oxidative cross-coupling is a robust method for forming C-C, C-X, and X-Y bonds. Organic electrosynthesis is recognized as an environmentally friendly and powerful synthetic platform. Recent advancements have shown that radical-involved electrochemical oxidative cross-coupling reactions can be achieved under exogenous-oxidant-free conditions.

CHEMICAL SOCIETY REVIEWS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents

Jonathan D. Bell et al.

Summary: This review explores the progress of photoredox chemistry with organic or transition metal agents, focusing on recent examples of bond formations using radical intermediates. The emphasis is on developments in the past 10 years, highlighting advances in transition metal and organic photoredox reagents chemistry.

CHEMICAL SOCIETY REVIEWS (2021)

添加到收藏夹

Article Chemistry, Physical

Mesoionic carbene-Breslow intermediates as super electron donors: Application to the metal-free arylacylation of alkenes

Wei Liu et al.

Summary: The newly discovered triazolylidenes mesoionic carbene have strong reducing ability, allowing them to undergo single-electron transfer with iodoarenes and efficiently catalyze arylacylation reactions on alkenes.

CHEM CATALYSIS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Persistent Radical Effect in Organic Synthesis

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Radical Acylfluoroalkylation of Olefins through N-Heterocyclic Carbene Organocatalysis

Jun-Long Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Organic

NHC-Catalyzed Radical Trifluoromethylation Enabled by Togni Reagent

Bei Zhang et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Bifunctional N-Heterocyclic Carbenes Derived from L-Pyroglutamic Acid and Their Applications in Enantioselective Organocatalysis

Xiang-Yu Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Multidisciplinary

Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides

Huan-Ming Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Physical

Catalytic radical generation of π-allylpalladium complexes

Huan-Ming Huang et al.

NATURE CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Organic

N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Synthesis of δ-Ketocarbonyls

Kenji Ota et al.

ORGANIC LETTERS (2020)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

Triplet Energy Transfer Photocatalysis: Unlocking the Next Level

Felix Strieth-Kalthoff et al.

CHEM (2020)

添加到收藏夹

Article Chemistry, Physical

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

Hirohisa Ohmiya

ACS CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Physical

Direct Synthesis of Dialkyl Ketones from Aliphatic Aldehydes through Radical N-Heterocyclic Carbene Catalysis

Yuki Kakeno et al.

ACS CATALYSIS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C-N, C-C, and C-O Bonds

Remi Blieck et al.

CHEMICAL REVIEWS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Transition metal-catalysed allylic functionalization reactions involving radicals

Huan-Ming Huang et al.

CHEMICAL SOCIETY REVIEWS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Allylic C(sp3)-H alkylation via synergistic organo- and photoredox catalyzed radical addition to imines

Jiaqi Jia et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts

Inwon Kim et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in N-heterocyclic carbene-based radical catalysis

Takuya Ishii et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes

Guanlin Li et al.

CHEMICAL SOCIETY REVIEWS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

Takuya Ishii et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Alienation of Terminal Alkynes with Aldehydes and Ketones

Xin Huang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

添加到收藏夹

Editorial Material Chemistry, Multidisciplinary

N-Heterocyclic Carbene Catalyzed Radical Coupling of Aldehydes with Redox-Active Esters

Runjiang Song et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Physical

Visible-Light Photoredox Enables Ketone Carbonyl Alkylation for Easy Access to Tertiary Alcohols

Minh Duy Vu et al.

ACS CATALYSIS (2019)

添加到收藏夹

Article Multidisciplinary Sciences

Site-specific allylic C-H bond functionalization with a copper-bound N-centred radical

Jiayuan Li et al.

NATURE (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes

Lu Liu et al.

CHEMICAL REVIEWS (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of gamma-butyrolactones

Kathleen J. R. Murauski et al.

CHEMICAL SOCIETY REVIEWS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective 1,2-Difunctionalization of 1,3-Butadiene by Sequential Alkylation and Carbonyl Allylation

Yang Xiong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Energy transfer catalysis mediated by visible light: principles, applications, directions

Felix Strieth-Kalthoff et al.

CHEMICAL SOCIETY REVIEWS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones

Anna Lucia Berger et al.

CHEMICAL SCIENCE (2018)

添加到收藏夹

Article Chemistry, Organic

Recent advances in the functionalization of allenes via radical process

Guanyinsheng Qiu et al.

TETRAHEDRON (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

The recent achievements of redox-neutral radical C-C cross-coupling enabled by visible-light

Jin Xie et al.

CHEMICAL SOCIETY REVIEWS (2017)

添加到收藏夹

Review Chemistry, Medicinal

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Minghao Feng et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2016)

添加到收藏夹

Review Chemistry, Applied

Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations

Kip Teegardin et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in employing homoenolates generated by N-heterocyclic carbene (NHC) catalysis in carbon-carbon bond-forming reactions

Rajeev S. Menon et al.

CHEMICAL SOCIETY REVIEWS (2015)

添加到收藏夹

Article Multidisciplinary Sciences

The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis

James D. Cuthbertson et al.

NATURE (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Redox-Neutral α-Allylation of Amines by Combining Palladium Catalysis and Visible-Light Photoredox Catalysis

Jun Xuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Cyclization Reactions of Allenes in the Presence of Unsaturated Carbon-Carbon Bonds

Juntao Ye et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

添加到收藏夹

Review Multidisciplinary Sciences

An overview of N-heterocyclic carbenes

Matthew N. Hopkinson et al.

NATURE (2014)

添加到收藏夹

Article Chemistry, Applied

Cooperative N-Heterocyclic Carbene (NHC) and Ruthenium Redox Catalysis: Oxidative Esterification of Aldehydes with Air as the Terminal Oxidant

Junfeng Zhao et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Bottleable (Amino)(Carboxy) Radicals Derived from Cyclic (Alkyl)(Amino) Carbenes

Janell K. Mahoney et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Multidisciplinary Sciences

Photoredox Activation for the Direct β-Arylation of Ketones and Aldehydes

Michael T. Pirnot et al.

SCIENCE (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

Shichao Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Organocatalytic umpolung: N-heterocyclic carbenes and beyond

Xavier Bugaut et al.

CHEMICAL SOCIETY REVIEWS (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO

Joyram Guin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

添加到收藏夹

Review Chemistry, Multidisciplinary

Stereocontrolled synthesis of tetrasubstituted olefins

Alison B. Flynn et al.

CHEMICAL REVIEWS (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate

MB Andrus et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

添加到收藏夹

Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

相关参考文献

导出引文

分享论文