264882-04-4Relevant articles and documents
Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates
Yang, Jingya,Wang, Ganggang,Zhou, Hongyan,Li, Zhifeng,Ma, Ben,Song, Menghui,Sun, Rongxia,Huo, Congde
supporting information, p. 394 - 398 (2021/01/29)
A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is
Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation
Cheng, Xiao,Cai, Bao-Gui,Mao, Hui,Lu, Juan,Li, Lei,Wang, Kun,Xuan, Jun
supporting information, p. 4109 - 4114 (2021/05/26)
We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.
Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents
Ye, Cong,Cai, Bao-Gui,Lu, Juan,Cheng, Xiao,Li, Lei,Pan, Zhong-Wen,Xuan, Jun
, p. 1012 - 1022 (2021/01/09)
A blue-light-emitting diode (LED) promoted coupling of aryl diazoacetates with sulfur ylides is described. This protocol features mild conditions, good functional group tolerance, and broad substrate scope for both aryl diazoacetates with sulfur ylides. Under optimal reaction conditions, a wide range of trisubstituted olefins is obtained in moderate to good yield, which can be further transferred to other biologically important heterocycles after a two-step simple operation.
Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives
Zhou, Shuangjing,Cai, Baogui,Hu, Chuxia,Cheng, Xu,Li, Lei,Xuan, Jun
supporting information, p. 2577 - 2581 (2021/03/22)
A visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates is developed. This one-pot two step reaction offers a mild and efficient approach for the synthesis of biologically important 2,3-dihydrobenzofuran derivatives in good yields and moderate diastereoselectivities.
Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters
Chu, Changhu,Dong, Wenwen,Lin, Jia,Teng, Jiangge,Wang, Zhiwei,Zhao, Rong
, p. 6120 - 6126 (2021/07/21)
By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.
Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil
supporting information, p. 6709 - 6713 (2021/09/08)
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.
Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
da Silva, Amanda F.,Afonso, Marco A. S.,Cormanich, Rodrigo A.,Jurberg, Igor D.
supporting information, p. 5648 - 5653 (2020/04/22)
A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
Diazo Activation with Diazonium Salts: Synthesis of Indazole and 1,2,4-Triazole
Li, Xuming,Ye, Xiaohan,Wei, Chiyu,Shan, Chuan,Wojtas, Lukasz,Wang, Qilin,Shi, Xiaodong
supporting information, p. 4151 - 4155 (2020/06/05)
A donor/acceptor diazo activation strategy, processing via condensation using diazonium salts without the addition of any other catalysts or reagents, is reported. The diazenium intermediate was found to undergo cyclization to give indazoles in excellent yields. Alternatively, in the presence of nitriles, substituted 1,2,4-triazoles were obtained in good to excellent yields. This interesting diazenium route provides a new approach to achieve complex heterocycle synthesis under mild conditions.
Catalyst-free, visible-light-promoted S-H insertion reaction between thiols and α-diazoesters
Chen, Shuwen,Huo, Congde,Liu, Cai,Ma, Ben,Song, Menghui,Wang, Ganggang,Yang, Jingya,Zhou, Hongyan
supporting information, p. 9494 - 9498 (2020/12/15)
A visible-light-promoted S-H insertion reaction between thiols and α-diazoesters was developed. The reaction proceeded smoothly at room temperature with a broad substrate scope, affording various thioethers in moderate to excellent yields. The catalyst- A
Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O
Thurow, Samuel,Fernandes, Alessandra A. G.,Quevedo-Acosta, Yovanny,De Oliveira, Matheus F.,De Oliveira, Marcelo G.,Jurberg, Igor D.
supporting information, p. 6909 - 6913 (2019/09/12)
A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.
