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Article
Chemistry, Multidisciplinary
Rongxiang Chen et al.
Summary: A cobalt-catalyzed esterification-peroxidation was developed for the synthesis of alpha-acyloxy esters from easily available starting materials. The reaction involved O-H insertion, C-H activation, and peroxidation reactions, and was found to proceed via a free-radical process.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Meng-Ling Lin et al.
Summary: Despite the existence of many studies on benzofuran-derived azadienes, there have been few reports on multi-component studies on this heterocyclic skeleton. This paper presents the first cascade three-component acyloxylation of diazo compounds with acids and azadienes under mild conditions. The reaction is applicable to various (A/A) diazo compounds, resulting in the generation of diverse complex benzofuran derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chuan Wan et al.
Summary: Visible-light-mediated methods for cysteine-selective bioconjugation suffer from bio-incompatible conditions and slow kinetics. Here, we report a transition metal-free thiol-sulfoxonium ylide photo-click reaction that enables bioconjugation under bio-compatible conditions. It demonstrates high cysteine-selectivity and rapid reaction kinetics using riboflavin derivatives as photocatalysts. This method provides efficient tools for exploring the druggable content of the human proteome.
Article
Chemistry, Organic
Yougen Xu et al.
Summary: In this study, a highly selective O-H bond insertion reaction of carboxylic acids and sulfoxonium ylides catalyzed by iridium(I) was developed using high-throughput experimentation and machine learning technologies. This reaction efficiently produces various (hetero)carboxymethyl ketones and is compatible with amine, phenol, alcohol, and free indole functional groups. Extensive exploration of the reaction space was also accomplished.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Gleb D. Titov et al.
Summary: An orthogonal reactivity of diazo compounds toward azirine-2-carboxylic acids, switching with the reaction conditions, is demonstrated. A gold-catalyzed reaction is N-selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O-H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metal-bound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.
Article
Chemistry, Multidisciplinary
Claire Empel et al.
Summary: This article provides a concise overview of photolysis reactions of diazoalkanes in photochemistry. It covers the discoveries in physical organic chemistry, examples of singlet carbene intermediates in organic synthesis, advances in cascade reactions and unusual protonation reactions under photochemical conditions. It also discusses the electronic control of singlet and triplet carbene intermediates and the recent advances in using weakly colored diazoalkanes in dye-sensitized reactions to access radical or triplet carbene intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Philip R. D. Murray et al.
Summary: This article presents a comprehensive review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCET involves the simultaneous exchange of an electron and a proton in a non-classical redox mechanism, offering opportunities for the direct generation of synthetically useful free radical intermediates from common organic functional groups. The article provides an introduction to MS-PCET and a practitioner's guide to reaction design, focusing on the unique energetic and selectivity features of this reaction class. It also discusses various oxidative and reductive PCET activations for bond homolysis and the applications of MS-PCET in asymmetric catalysis, materials, and device applications.
Article
Chemistry, Multidisciplinary
Clarice A. D. Caiuby et al.
Summary: Sulfoxonium ylides are important surrogates for diazo compounds, known for their bench stability and handling advantages. While they have been used in a variety of novel chemical reactions in recent years, efficient asymmetric transformations, specifically catalytic enantioselective versions, have only recently been reported, highlighting existing challenges in this area.
Article
Chemistry, Multidisciplinary
Jiawen Lang et al.
Summary: An efficient asymmetric synthesis of isochromanone derivatives was achieved through Z-selective 1,3-OH insertion/aldol cyclization reaction using acyclic carboxylic oxonium ylides. The use of specific chiral catalysts and substrates enabled the cascade reaction with good stereochemistry control. This strategy provides a practical approach to access benzo-fused delta-lactones with vicinal quaternary stereocenters.
Article
Chemistry, Organic
Sivasankar Koothradan et al.
Summary: Functionalization of carboxylic acids using sulfoxonium ylides in the presence of [VO(acac)(2)] as a catalyst is reported. Compared to the usual carbene source, diazo compounds, sulfoxonium ylides were found to produce alpha-carbonyloxy esters in better yield. Various standard spectroscopic and analytical techniques were utilized to characterize the formed products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hosam Choi et al.
Summary: This report presents a highly efficient approach for the synthesis of beta,gamma-disubstituted gamma-butyrolactone motifs. The approach combines diastereoselective aldol and nickel carbene-mediated gamma-butyrolactonization, and utilizes intramolecular ring closure to rapidly synthesize a range of functionalized chiral ybutyrolactones. This single-step method has been applied to synthesize natural products and organic compounds, including (-)-talaumidin methyl ether, (+)-veraguensin, (+)-dubiusamine A, and (+)-phaseolinic acid, and is considered one of the shortest syntheses reported to date.
Article
Chemistry, Organic
Radell Echemendia et al.
Summary: A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides.
Review
Chemistry, Organic
Zhang Jianto et al.
Summary: This article systematically summarizes the high stability and diverse reactivity of sulfoxonium ylides as powerful reagents in organic synthesis. It focuses on the new methods and progress of utilizing sulfoxonium ylides as important synthons to construct nitrogen-containing heterocyclic compounds, such as pyrrole, imidazole, indole, quinoline, quinoxaline, and cinnoline. The future development trend of green synthesis of nitrogen heterocycles from sulfoxonium ylides is also discussed.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Robin Tyburski et al.
Summary: Proton-coupled electron transfer (PCET) reactions play a fundamental role in energy transformation reactions and are increasingly important in catalysis and synthetic chemistry. The interplay between proton and electron transfer leads to a richness of reactivity, with various sequential and concerted mechanisms. Understanding and distinguishing between different PCET mechanisms is crucial for the design and optimization of reactions utilizing PCET.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Claire Empel et al.
Summary: In this study, a nonbenzenoid aromatic carbocation, tropylium, was utilized as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids, showing excellent efficiency across a wide range of substrates.
Review
Chemistry, Organic
Zijie Zhou et al.
Summary: Proton-coupled electron transfer (PCET) reactions are unconventional redox reactions with special reactivities and selectivities due to their unique interdependent electron-proton transfer mechanisms. These reactions play a key role in organic synthesis, and through electrochemical and photochemical methods, various activation reactions have been achieved, leading to the synthesis of important structures and fundamental frameworks.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yangxiu Mu et al.
Review
Chemistry, Organic
Giorgiana Denisa Bisag et al.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Review
Chemistry, Multidisciplinary
Zhen Yang et al.
CHEMICAL SOCIETY REVIEWS
(2020)
Review
Chemistry, Organic
Yuan-Yuan Ren et al.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Igor D. Jurberg et al.
Article
Chemistry, Multidisciplinary
James D. Neuhaus et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Applied
Yiliang Zhang et al.
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Review
Chemistry, Multidisciplinary
Liang-Qiu Lu et al.
CHEMICAL SOCIETY REVIEWS
(2017)
Review
Chemistry, Multidisciplinary
Emily C. Gentry et al.
ACCOUNTS OF CHEMICAL RESEARCH
(2016)
Review
Biochemistry & Molecular Biology
Kalie A. Mix et al.
ACS CHEMICAL BIOLOGY
(2016)
Article
Chemistry, Organic
Arianne C. Hunter et al.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Physical
Fei Tan et al.
Review
Chemistry, Multidisciplinary
Alan Ford et al.
Article
Chemistry, Multidisciplinary
Zikun Wang et al.
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Multidisciplinary
Mitsuru Kitamura et al.
Article
Chemistry, Multidisciplinary
Erik Kuehnel et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2007)
Article
Chemistry, Organic
S Bertelsen et al.
SYNTHESIS-STUTTGART
(2005)
Article
Chemistry, Organic
N Jiang et al.
TETRAHEDRON LETTERS
(2001)
