64464-76-2Relevant academic research and scientific papers
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
, 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
Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides
Lu, Juan,Li, Lei,He, Xiang-Kui,Xu, Guo-Yong,Xuan, Jun
, p. 1646 - 1650 (2021/05/28)
A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.
Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source
Shen, Guoli,Liu, Haojie,Chen, Jingchao,He, Zhenxiu,Zhou, Yongyun,Wang, Lin,Luo, Yang,Su, Zhimin,Fan, Baomin
, p. 3601 - 3610 (2021/05/04)
The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is
Visible-light-promoted nitrone synthesis from nitrosoarenes under catalyst- and additive-free conditions
Cai, Bao-Gui,Li, Lin,Xiao, Wen-Jing,Xu, Guo-Yong,Xuan, Jun
, p. 823 - 829 (2021/06/15)
A green and sustainable nitrone formation reaction via visible-light-promoted reaction of aryl diazoacetates with nitrosoarenes is described. This protocol exhibits good functional group tolerance and broad substrate scope for both aryl diazoacetates with nitrosoarenes. Comparing the reported methods for the synthesis of nitrones from nitrosoarenes, the reaction described herein occurs under sole visible-light irradiation without the need of any catalysts and additives. Graphic abstract: [Figure not available: see fulltext.]
Blue light-promoted cyclopropenizations of N-tosylhydrazones in water
Yan, Kaichuan,He, Hua,Li, Jianglian,Luo, Yi,Lai, Ruizhi,Guo, Li,Wu, Yong
supporting information, p. 3984 - 3987 (2021/06/15)
Carbene transfer reactions play an important role in the field of organic synthesis because of their ability to construct a variety of molecules. Herein, we reported on blue light-induced cyclopropenizations of N-tosylhydrazones in water, which avoids the use of expensive metal-based catalysts and toxic organic solvents. This metal-free and operationally simple methodology enable highly efficient cyclopropenizations, X-H insertion reactions, and cyclopropanation under mild reaction conditions.
Well-Defined, Versatile and Recyclable Half-Sandwich Nickelacarborane Catalyst for Selective Carbene-Transfer Reactions
Wang, Linghua,Perveen, Saima,Ouyang, Yizhao,Zhang, Shuai,Jiao, Jiao,He, Gang,Nie, Yong,Li, Pengfei
supporting information, p. 5754 - 5760 (2021/03/08)
Catalytic carbene-transfer reactions constitute a class of highly useful transformations in organic synthesis. Although catalysts based on a range of transition-metals have been reported, the readily accessible nickel(II)-based complexes have been rarely used. Herein, an air-stable nickel(II)-carborane complex is reported as a well-defined, versatile and recyclable catalyst for selective carbene transfer reactions with low catalyst loading under mild conditions. This catalyst is effective for several types of reactions including diastereoselective cyclopropanation, epoxidation, selective X?H insertions (X = C, N, O, S, Si), particularly for the unprotected substrates. This represents a rare example of carborane ligands in base metal catalysis.
TfOH-Catalyzed N-H Insertion of α-Substituted-α-Diazoesters with Anilines Provides Access to Unnatural α-Amino Esters
Hu, Sha,Wu, Jiale,Lu, Zuolin,Wang, Jiaqi,Tao, Yuan,Jiang, Meifen,Chen, Fener
, p. 3223 - 3231 (2021/02/05)
A time-economical TfOH-catalyzed N-H insertion between anilines and α-alkyl and α-aryl-α-diazoacetates provides a straightforward approach to access unnatural α-amino esters, which readily undergo various transformations and can thus be used for the synthesis of pharmaceutically relevant molecules. The α-amino esters were obtained in moderate to excellent yields.
Visible-Light-Mediated Strategies to Assemble Alkyl 2-Carboxylate-2,3,3-Trisubstituted β-Lactams and 5-Alkoxy-2,2,4-Trisubstituted Furan-3(2H)-ones Using Aryldiazoacetates and Aryldiazoketones
Deflon, Victor M.,Dos Santos, Caio Y.,Gallo, Rafael D. C.,Jurberg, Igor D.,Munaretto, Laiéli S.,Okada, Celso Y.
supporting information, p. 9292 - 9296 (2021/12/06)
Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3
Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides
Burtoloso, Antonio C. B.,Echemendía, Radell,Furniel, Lucas G.
, p. 7453 - 7459 (2021/06/09)
The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. By way of a catalytic asymmetric insertion reaction into N-H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven α-arylglycine esters were synthesized in enantiomeric ratios up to 92?:?8 (99?:?1 after a single recrystallization) and reaction yields ranging between 49-96%. Furthermore, the protocol benefits from quick reaction times and is conducted in a straightforward manner.
Blue Light-promoted Carbene Transfer Reactions of Tosylhydrazones
Xu, Yingying,Lv, Guanghui,Yan, Kaichuan,He, Hua,Li, Jianglian,Luo, Yi,Lai, Ruizhi,Hai, Li,Wu, Yong
supporting information, p. 1945 - 1947 (2020/06/08)
Metal-free photochemical carbene-transfer reactions of tosylhydrazones were developed under blue light irradiation at room temperature. This reaction constructs C?X (X=C, N, O, S) bonds and cyclopropanes from readily available and stable starting material
