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Review
Chemistry, Physical
Wei Xiao et al.
Summary: Radical covalent catalysis, achieved through a radical catalyst addition and elimination process, has made significant progress in the past few decades. This review aims to summarize recent advances in radical covalent catalysis, highlight major challenges, and identify potential areas for improvement, providing inspiration for future studies.
Article
Chemistry, Multidisciplinary
Jiang-Ling Shi et al.
Summary: This study demonstrates the generation of alkoxy radicals through visible-light-induced electron transfer and their subsequent transformation into carbon-centered radicals. The compatibility of this method with various carbon radical trapping processes opens up new possibilities for the application of alkoxy radicals in organic synthesis.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuai Liu et al.
Summary: This study describes a concise Fe-catalyzed alkylazidation of alpha-trifluormethylalkenes via a C-C bond cleavage/radical addition/azidation cascade. The protocol offers a practical and step-economic approach to the synthesis of tertiary alpha-trifluoromethyl azides, with broad substrate scope, excellent functional group compatibility, and the ability to be performed on a gram scale.
Article
Chemistry, Organic
Tian-Yu Zhang et al.
Summary: An inexpensive iron-catalyzed alkoxylradical-induced C-C bond cleavage/gem-difluoroalkylation cascade is developed. Fluorinated distal diketones are synthesized via a ring-opening strategy regulated by the structure of alkoxyl radical precursors, while difluoroalkylated medium-sized lactones and macrolactones are constructed through a ring-expansion strategy. Both protocols show mild and redox neutral conditions, broad substrate scope, and good functional group compatibility.
Article
Chemistry, Organic
Shuji Nagano et al.
Summary: We describe a photochemical method for generating alkyl radicals from alkylsilyl peroxides (ASPs) without the need for any transition metal or photocatalyst. This simple protocol uses Hantzsch ester as a photoreductant to efficiently cleave the O-O bond of various ASPs via single-electron transfer and produce corresponding alkyl radicals under mild conditions. These radicals can then undergo Giese-type addition reactions with a wide range of electron-deficient alkenes. This study expands the methods for generating radicals from ASPs and enhances their applicability and versatility in radical chemistry.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Jeremy H. Dworkin et al.
Trends in Chemistry
(2023)
Review
Chemistry, Multidisciplinary
Peng-Zi Wang et al.
Summary: The C-O bond is important due to its presence in biologically active molecules, pharmaceutical agents, and functional materials. Traditional methods involving strong base and acid have limitations, so the development of C-O bond-forming reactions using catalytic strategies is increasingly important. Copper-promoted radical-mediated C-O bond formation is gaining research interest due to advancements in free-radical chemistry and photoredox catalysis. This Perspective highlights and evaluates state-of-the-art techniques in this field, organized by reaction types and working models.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Physical
Liuzhen Hou et al.
Summary: Visible light-induced photocatalysis has been widely studied for building new catalytic platforms that are unattainable under ground state conditions. Asymmetric photocatalysis remains a challenge due to the high reactivity of photogenerated intermediates. This review summarizes recent advancements in the photocatalytic asymmetric transformations of carbonyl compounds for synthesizing chiral alcohols.
Review
Chemistry, Multidisciplinary
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.
Article
Chemistry, Organic
Haiyan Dong et al.
Summary: In this study, cycloalkyl silyl peroxides (CSP) were successfully utilized as electrophilic coupling partners in cross-electrophile coupling reactions for the first time. Diverse CSP compounds were efficiently cross-coupled with a range of alpha-trifluoromethyl alkenes under nickel catalysis with zinc as a reducing agent, leading to the synthesis of gem-difluoroalkenes with a pendent ketone moiety and excellent functionality tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wenfeng Zhong et al.
Summary: In this study, alkylsilyl peroxides were generated in situ from organosilicon compounds and an amine base. The alkylsilyl peroxides were then cleaved by copper catalysis to produce alkyl radicals, which reacted with nucleophiles to form coupling products with new carbon-carbon, carbon-nitrogen, or carbon-halogen bonds.
Article
Chemistry, Organic
Ming-Hua Wang et al.
Summary: An efficient iron-catalyzed allylation reaction of cycloalkyl hydroperoxides with allylic sulfones via C-C bond cleavage has been developed. This protocol provides an efficient method for the synthesis of distally allylated ketones with good functional group tolerance and high regioselectivity under redox-neutral conditions. Preliminary mechanistic studies suggest the involvement of a radical process in this reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Weiping Xu et al.
Summary: It has been discovered that under mild reaction conditions, two carbon-carbon bonds can be formed using vinylarenes, alkylsilyl peroxides, and beta-keto carbonyl substrates with the presence of catalytic Fe(OTf)2.
Article
Chemistry, Multidisciplinary
Huimin Yu et al.
Summary: In this study, the use of synergistic Pd/Cu catalysis in the photochemical 1,4-bisalkylation reactions was reported, resulting in the efficient synthesis of α-amino acid esters bearing quaternary stereocenters. Experimental and computational investigation confirmed a radical pathway involving catalysis by an excited-state palladium species, with the stereochemistry mainly controlled by the chiral Cu catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Hanbin Lu et al.
Summary: A three-component coupling reaction of α, β, γ, δ-unsaturated carbonyl compounds with alkylsilyl peroxides catalyzed by Fe(OTf)(2) under mild reaction conditions is achieved in the presence of certain heteronucleophiles (ROH and indole). Various α, β, γ, δ-diene carbonyl substrates with different substituents can be successfully employed by combining them with different alkylsilyl peroxides. This new approach is also applicable to the double functionalization of diene substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bin Lu et al.
Summary: Photoredox catalysis is utilized to regulate amine coupling partners and drive switchable radical carbonylation reactions. This strategy enables the selective formation of valuable carbonyl compounds, including amides and α-ketoamides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jie Wei et al.
Summary: An enantioselective three-component rearrangement of alkenylfurans has been developed by merging photoredox catalysis with chiral Brønsted acid catalysis. This protocol provides expedient access to a broad spectrum of ketoalkyl-functionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities. Diverse functional groups can be introduced via facile product derivations.
Article
Chemistry, Organic
Mi Zhou et al.
Summary: A novel approach for constructing alpha-quaternary carbon centers using an Fe(II)-catalyzed alkylation reaction between alpha-alkoxy-1,3 dicarbonyl compounds and various alkylsilyl peroxides has been developed. This strategy enables the use of a broad range of 1,3 dicarbonyl derivatives and alkylsilyl peroxides as substrates, and involves a radical-promoted reaction pathway.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Physical
Peng-Zi Wang et al.
Summary: Atom transfer radical addition (ATRA) reaction of alkenes has a significant impact in the field of radical difunctionalization of alkenes. A novel copper-catalyzed asymmetric three-component photo-ATRA-type reaction is reported, which enables highly enantioselective intermolecular C-O cross-coupling between carbon radicals and carboxylic acids.
Article
Chemistry, Multidisciplinary
Guoqing Li et al.
Summary: In this study, a highly efficient, selective and atom-economical method for the construction of allylic amines is reported. The combination of a photoredox catalyst and cobaloxime catalyst enables site-selective allylic amination of various olefins with secondary alkyl amines, resulting in valuable tertiary aliphatic allylamines without the need for external oxidants.
GREEN SYNTHESIS AND CATALYSIS
(2022)
Review
Chemistry, Multidisciplinary
Xiao-Ye Yu et al.
Summary: In recent years, visible light photoredox-catalyzed radical-mediated C-C bond cleavage reactions have emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C-C bond cleavage in diverse molecular scaffolds. These reactions provide an efficient way to construct structurally diverse molecular skeletons, contributing to the development in the field of synthetic organic chemistry.
Review
Chemistry, Multidisciplinary
Lei Dai et al.
Summary: N-heterocyclic carbene (NHC)-catalyzed reactions involving two-electron and radical pathways have been well-established, with the former more developed than the latter in terms of reaction types and enantioselectivity. In the past decade, several elegant NHC-catalyzed radical reactions have been developed, including oxidation of aldehydes, reductive coupling reactions, and reactions via radical homoenolates.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Akira Matsumoto et al.
Summary: This account discusses the development of efficient methods for generating alkyl radicals from organosilicon peroxides and their applications in selective alkylation reactions, providing a new pathway for the formation of various carbon-carbon and carbon-heteroatom bonds under mild conditions.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Organic
Weiping Xu et al.
Summary: The copper-catalyzed selective cleavage of alkylsilyl peroxides and subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds is described. The reaction proceeds under mild conditions and shows a broad substrate scope, particularly suitable for radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Mechanistic studies suggest a free-radical process is involved in the reaction.
Article
Multidisciplinary Sciences
Xiaotao Zhu et al.
Summary: The authors present a method to form chiral esters from conjugated dienes with copper and chiral PyBox ligands, likely proceeding via an allylic radical. This work represents an advance in the enantioselective construction of C-O bond on open-chain hydrocarbon radicals, which may lead to the discovery of other asymmetric radical reactions. The participation of external acids in the reaction substantially extends its applicability and leads to structurally diverse allylic ester products.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Applied
Shivani Sharma et al.
Summary: The novel concept of radical-polar crossover (RPCO) and polar-radical crossover (PRCO) reactions has emerged in recent years as a valuable tool bridging the gap between polar and radical reactions, overcoming their limitations, and improving the green quotient of reactions. The development and transformation of this area into synthetically important reactions is summarized in this review.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Peng-Zi Wang et al.
Summary: The radical vicinal dicarbofunctionalization (DCF) reaction of olefins by merging of radical addition and cross-coupling using photoredox and copper dual catalysis demonstrates high enantioselectivity and tolerance towards a wide range of functionalities. This protocol provides a valuable synthetic tool for the construction of optically active compounds with potential applications in organic synthesis.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Organic
Qing-Xin Sun et al.
Summary: A cost-effective iron-catalyzed method for C-C bond cleavage/thiolation and selenylation of cycloalkyl hydroperoxides is described, providing efficient access to a variety of distal keto-functionalized thioethers and selenium compounds, with only small amounts of disulfides needed for the transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Organic
Canhua Zhou et al.
Summary: A new approach has been developed for highly selective monoalkylation of active methylene and related derivatives using various types of alkylsilyl peroxides in the presence of copper catalysts under mild conditions. This method has a wide substrate scope involving both active methylene compounds and alkylsilyl peroxides, and it can also utilize nitroalkanes for copper-catalyzed selective monoalkylation. The mechanistic study suggests the involvement of radical species in the monoalkylation reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hong Xin et al.
Summary: A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides has been developed, providing a straightforward route to unnatural amino acids with a distal carbonyl group in moderate to good yields. Mechanistic studies indicate the involvement of both a SET event and radical chain propagation in this transformation.
Article
Chemistry, Multidisciplinary
Shuai Liu et al.
Summary: An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) as the reaction condition has been developed. This protocol features redox-neutral conditions, green halogen sources, and a broad substrate scope, providing practical access to distally chlorinated, brominated and iodinated alkyl ketones and alkyl nitriles with moderate to good yields.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Saori Tsuzuki et al.
Summary: This study describes a Ni-catalyzed direct C-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors. The reaction forms a new C(sp(3))-C(sp(2)) bond via selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-H bonds. Due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at the ortho-position of readily available N-quinolylbenzamide derivatives.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Na Chen et al.
Summary: There has been a resurgence of interest in organic electrochemistry as a green synthetic tool, with many electrochemical methods developed in the past decade to access various nitrogen-centered radicals (NCRs) for the construction of nitrogen-containing organic compounds. This review critically highlights recent advances in the chemistry of electrochemically generated NCRs, focusing on the strategies for their formation and types of NCRs, as well as the mechanism and synthetic applications of different NCRs.
GREEN SYNTHESIS AND CATALYSIS
(2021)
Article
Chemistry, Organic
Jiamin Lv et al.
Summary: A novel method for selectively monoalkylating active methylene compounds with various alkylsilyl peroxides under mild copper catalysis has been developed. Mechanistic studies suggest the involvement of radical species in this alkylation reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shunya Sakurai et al.
Summary: This study presents a Cu-catalyzed O-alkylation of phenol derivatives using alkylsilyl peroxides as alkyl radical precursors. The reaction proceeds smoothly under mild conditions and the use of two different ligands with a Cu catalyst provides a wide range of products. Mechanistic studies suggest that the reaction proceeds via a radical mechanism.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Brett N. Hemric
Summary: 1,2-Amino oxygenation is an important synthetic strategy for the synthesis of pharmaceuticals, natural products, and synthetic ligands, with a wide range of applications. Modern chemistry has developed a variety of novel methods for 1,2-amino oxygenation, such as using different transition metals and electrochemical, photochemical, and biochemical reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yoko Shiozaki et al.
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Review
Chemistry, Multidisciplinary
Rebecca J. Wiles et al.
ISRAEL JOURNAL OF CHEMISTRY
(2020)
Article
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Shunya Sakurai et al.
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Gregory J. P. Perry et al.
Article
Chemistry, Organic
Lei Chen et al.
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Shunya Sakurai et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Review
Chemistry, Multidisciplinary
Elaine Tsui et al.
Article
Chemistry, Multidisciplinary
Shuo Yang et al.
CHEMICAL COMMUNICATIONS
(2020)
Review
Chemistry, Multidisciplinary
Pengzi Wang et al.
GREEN SYNTHESIS AND CATALYSIS
(2020)
Review
Chemistry, Multidisciplinary
Zhong-Liang Li et al.
CHEMICAL SOCIETY REVIEWS
(2020)
Article
Chemistry, Organic
Takumi Seihara et al.
Article
Chemistry, Organic
Pin Gao et al.
Article
Chemistry, Organic
Shunya Sakurai et al.
Review
Chemistry, Multidisciplinary
Lena Pitzer et al.
Article
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Jun-Cheng Yang et al.
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Multidisciplinary
Yang Xiong et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Ryu Sakamoto et al.
Article
Chemistry, Organic
Yang Xiong et al.
TETRAHEDRON LETTERS
(2018)
Review
Chemistry, Multidisciplinary
Fei Wang et al.
ACCOUNTS OF CHEMICAL RESEARCH
(2018)
Article
Chemistry, Applied
Xiao-Ye Yu et al.
ADVANCED SYNTHESIS & CATALYSIS
(2018)
Article
Chemistry, Multidisciplinary
Xiao-Ye Yu et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Xiao-Ye Yu et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Ryu Sakamoto et al.
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Review
Chemistry, Multidisciplinary
Ming Yan et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Organic
Baoguo Zhao et al.
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Organic
Haifeng Du et al.
