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Article
Chemistry, Multidisciplinary
Zhiwei Wang et al.
Summary: A facile and environmentally friendly visible-light-induced three-component reaction of alpha-diazoesters, cyclic ethers, and NaSCN has been developed to construct organic thiocyanates at room temperature. The reaction proceeds under photocatalyst-and additive-free conditions, yielding a number of organic thiocyanates with moderate to good yield and favorable functional group tolerance.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Applied
Yan-Rui Zhao et al.
Summary: A new method for the construction of all-carbon tetra-substituted olefins using visible-light promoted coupling of diazo compounds with iodonium ylides has been developed, resulting in a wide range of products in moderate to good yields. The synthetic value of this method was demonstrated through the synthesis of natural isolates modified alkenes and the successful transformation of final olefins into important heterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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)
Article
Chemistry, Organic
Mateus L. Stivanin et al.
Summary: A blue light-promoted reaction has been developed, which allows the incorporation of aryldiazoacetates and different nucleophiles into a single product using THF (and other cyclic ethers) as the solvent. This transformation represents an O-H insertion strategy of complex alcohols into aryldiazoesters without pre-assembling. The method is mild and efficient, and can proceed at room temperature without the need for metals.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ya-Nan Wang et al.
Summary: Theoretical investigation of carbene-enabled ether activation revealed that the final products were dependent on the stability of the oxonium intermediate, achieved through nucleophilic attack of ethers onto carbene species. The nucleophilicity of ethers was found to be crucial for polarization and charge transfer, influencing the chemoselectivity of the reaction. Surprisingly, solvation of ethers did not play a significant role in determining the outcome of the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Heyun Sheng et al.
Summary: An unprecedented difluorocarbene-mediated C-O bond cleavage of cyclic ethers for the construction of difluoromethyl ethers is described. This protocol offers mild conditions, high efficiency, and a wide substrate scope, allowing for the tolerance of sensitive functional groups and complex molecules. It shows excellent chemoselectivities and has great potential for late-stage modification of pharmaceutical compounds and natural products.
Article
Chemistry, Organic
Chao Pei et al.
Summary: In this computational study, the authors analyze the reaction mechanism and observe the formation of a singlet carbene. Depending on the pKa value of the alcohol, this carbene can undergo direct protonation or enol formation to yield different products. Propargylic alcohols, on the other hand, form a complex with the carbene intermediate, leading to facile cyclopropenation reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ze-Le Chen et al.
Summary: A site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical carbene transfer reactions is reported in this study. The approach can also be extended to the difunctionalization of NHC-boranes through cyclopropanation and the B-H insertion reaction. Further investigations on photochemical continuous-flow applications and synthetic transformations demonstrate the utility of the method. Theoretical calculations and control experiments were conducted to explain the observed selectivity.
Article
Chemistry, Organic
Jiupeng Liu et al.
Summary: A visible-light-induced C-Br bond homolysis of bromomalonates has been developed, providing an efficient approach for the synthesis of carbonylated and hydroxylated benzofurans from 1,6-enynes under mild conditions, without the need for transition metals, photocatalysts, oxidants, or additives. Mechanistic studies suggest an energy-transfer pathway for the C-Br bond homolysis, with atom-transfer radical addition products serving as key intermediates for the generation of carbonylated and hydroxylated benzofurans.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jiaqi Li et al.
Summary: A visible light-promoted radical-mediated ring-opening/cyclization of vinyl benzotriazoles has been developed for the synthesis of functionalized phenanthridines from alkyl bromides. The readily available and bench-stable vinyl benzotriazoles serve as valuable alternative radical acceptors during the synthesis of phenanthridines.
Article
Chemistry, Organic
Keyong Zhu et al.
Summary: This study developed a method for the visible light-promoted generation of nitrilium ions from diazoacetates and nitriles. The reaction involves the transformation of diazoacetates to free carbenes under visible light, which are then trapped by nitriles to generate nitrilium ions. Nitrilium ions undergo nucleophilic attack on benzotriazoles and carboxylic acids to produce N-imidoylbenzotriazoles and diacylglycine esters in good to excellent yields.
Article
Chemistry, Organic
Chengming Qu et al.
Summary: A simple visible-light-initiated strategy was developed for the synthesis of organophosphorus compounds via a multicomponent reaction. This method offers mild reaction conditions, easy operation, good functional group tolerance, and the ability for gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bao-Gui Cai et al.
Summary: In this study, a visible-light-promoted three component reaction was reported, which enables the efficient synthesis of a variety of imide products. Furthermore, the synthetic application of these imide products for the synthesis of isoquinoline-1,3(2H,4H)-dione derivatives was demonstrated.
Article
Chemistry, Organic
Yantao Liu et al.
Summary: This study developed a visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite, providing an efficient approach to gamma-oximino esters under mild conditions. The transformation not only demonstrated the good compatibility of nucleophilic diazo compounds and electrophilic tert-butyl nitrite, but also revealed the preference of alkyl radicals generated by diazo compounds for addition to alkenes over nitroso radicals.
Article
Chemistry, Physical
Bao-Gui Cai et al.
Summary: In this study, we reported the visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent carbene transfer reactions. Two kinds of important hydroxamic acid esters were obtained in good yields under optimized reaction conditions depending on the reaction media used. The utility and practicality of this method were demonstrated through mild reaction conditions, excellent functional group tolerance, useful synthetic transformations, and successful modification of natural products and drug molecules.
Review
Chemistry, Organic
Xie Yang et al.
Summary: This review summarizes the recent developments in the photocatalytic generation of radicals from diazo compounds, including the formation of diazomethyl radicals, carbon radicals, carbyne radicals, and allene radicals. Additionally, the future development direction and challenges in this field are prospected.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Li Sen et al.
Summary: Diazo compounds are important synthetic intermediates and their combination with visible-light photoredox catalysis has allowed the development of novel reactions, expanding their synthetic applications.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chengming Qu et al.
Summary: A metal-free strategy using visible-light-driven four-component reactions has been developed to construct S-alkyl phosphorothioates. This method utilizes DBU as an additive and elemental sulfur as a cheap and odorless sulfur source, providing an efficient approach to access various S-alkyl phosphorothioates under mild conditions. Additionally, three-component coupling products can be obtained conveniently by changing the reaction solvent.
Article
Chemistry, Organic
Yufen Lv et al.
Summary: This article describes a metal-free and visible-light-promoted method for the synthesis of S-alkyl dithiocarbamates through multicomponent reactions. The transformation can be conveniently carried out at room temperature in air using DBU as the additive, generating nitrogen as the only side-product. Interestingly, the reaction of alpha-aryldiazoesters, amines, and CS2 in the presence of THF leads to the rapid and efficient formation of structurally diverse four-component coupling products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Mateus L. Stivanin et al.
Summary: Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates have been reported, leading to different products depending on the solvent used. One protocol involves direct O-H insertion in DCM, while the other incorporates the ring-opened form of THF into the product structure. These metal-free protocols are mild, tolerant to air and moisture, and have been demonstrated in the synthesis of an acaricide.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yantao Liu et al.
Summary: A mild and highly efficient approach to alkyl oxazoles has been reported, utilizing a combination of gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles can be synthesized with good to excellent yields and wide functional-group compatibility under blue-light irradiation. The copper catalyst plays a dual role in accelerating protodeauration of vinyl gold intermediates and enhancing photoredox catalysis in this transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sripati Jana et al.
Summary: Controlling the reactivity of diaryl carbenes can be achieved by manipulating the electronic properties of the substituents, allowing for highly chemoselective carbene transfer reactions without the need for external additives. Photolysis of diazo compounds can readily access the free diaryl carbenes, which can then undergo various chemoselective reactions. Experimental and theoretical analyses confirm the involvement of different carbene spin states in rationalizing the observed reactivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xiao Cheng et al.
Summary: The study developed a visible light-promoted divergent cycloaddition of alpha-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks with good yields by changing the reaction media. The reaction occurred solely under visible light irradiation without exogenous photoredox catalysts, and a reasonable reaction mechanism was proposed based on control experiments and density functional theory calculations.
Review
Chemistry, Multidisciplinary
Xiaotian Qi et al.
Summary: Metal carbenes play a crucial role in modern organic synthesis, and computational studies of their transformation reactions with different nucleophiles can provide valuable mechanistic insights for the design of new reactions. Three generalized reaction models for carbene transformation with nucleophiles are proposed based on our computational results: intramolecular migratory insertion of metal carbene, intermolecular nucleophilic addition towards metal carbene, and outer-sphere nucleophilic addition to metal-ligated free carbene.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Yantao Liu et al.
Summary: A gold-catalyzed synthesis of polyfluoroalkylated oxazoles from N-propargylamides under visible-light irradiation has been developed, showing excellent compatibility of radicals and gold catalysts. Mechanistic experiments revealed the dual role of polyfluoroalkyl iodides in enhancing compatibility and reactivation of the gold catalyst. Furthermore, PPh3AuNTf2 not only activates N-propargylamide to generate vinyl gold intermediate, but also promotes homolysis of polyfluoroalkyl iodides under blue light irradiation.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Qian Li et al.
Summary: A green and sustainable oxime ether formation method using visible light to promote the O-H functionalization of oximes with diazo esters is efficient and versatile, with high yields and tolerance to various functional groups. When a cyclic ether solvent is used, such as THF, 1,4-dioxane, and tetrahydropyran, an interesting photochemical three-component reaction product can be obtained in good yields.
Article
Chemistry, Multidisciplinary
Jakub Durka et al.
Summary: Diazo compounds are valuable reagents in organic synthesis, and their photochemical reactions under visible light irradiation offer sustainable and efficient alternatives to transition metal catalysis. These reactions have shown promising applications in various transformations, highlighting a potential future direction for greener synthetic methodologies.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Review
Chemistry, Organic
Cai Baogui et al.
Summary: The visible light-promoted transformation of diazo compounds through the formation of free carbene is a significant advancement in organic synthesis, aligning with the principles of green chemistry. Chinese research groups have made noteworthy contributions to this field, which is expected to continue to grow and face new challenges in the future.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ben Niu et al.
Summary: The light-promoted C-C bond forming reaction can yield sulfone and phosphate derivatives at room temperature without the need for metals or photoredox catalyst. This transformation proceeds through an auto-oxidation mechanism maintained by trace amounts of O-2 as the sole green oxidant.
Article
Chemistry, Multidisciplinary
Debajit Maiti et al.
Summary: In this study, a blue LED mediated reaction was reported using aryl diazoacetate, 1,4-dioxane/THP, and various heterocycles in water. The process involved oxonium ylides formation, amino etherification, [1,2] shift, and synthesis of 1,4,7-dioxazonan-6-ones. Reaction kinetics, Hammett's plot, and DFT calculations were used to rationalize the formation of ylides and subsequent reactions. The study demonstrated a sustainable process of converting toxic 1,4-dioxane in functionalizing heterocycles.
Article
Chemistry, Multidisciplinary
Weiyu Li et al.
Summary: This research reports a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, yielding various gamma-seleno allylic sulfones. The reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without the need for any photocatalysts or additives. Synthetic applications of the resulting products were demonstrated through deselenization, reduction, bromination, and allylation.
Article
Chemistry, Applied
Mateus L. Stivanin et al.
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Yujing Guo et al.
Article
Chemistry, Organic
Yantao Liu et al.
Review
Chemistry, Multidisciplinary
Zhen Yang et al.
CHEMICAL SOCIETY REVIEWS
(2020)
Article
Chemistry, Multidisciplinary
Feifei He et al.
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Ruixiang Cheng et al.
Article
Chemistry, Organic
Jingjing Zhao et al.
Article
Chemistry, Multidisciplinary
Rene Hommelsheim et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Review
Chemistry, Organic
Lukasz W. Ciszewski et al.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Feifei He et al.
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Sripati Jana et al.
Article
Chemistry, Multidisciplinary
Tiebo Xiao et al.
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Igor D. Jurberg et al.
Article
Multidisciplinary Sciences
Pan Li et al.
NATURE COMMUNICATIONS
(2018)
Review
Chemistry, Multidisciplinary
Ying Xia et al.
