13314-91-5Relevant academic research and scientific papers
The rhodium catalyzed three-component reaction of diazoacetates, titanium(IV) alkoxides and aldehydes
Lu, Chong-Dao,Liu, Hui,Chen, Zhi-Yong,Hu, Wen-Hao,Mi, Ai-Qiao
, p. 2624 - 2626 (2005)
The rhodium(n)-catalyzed three-component reaction of diazoacetates, titanium alkoxides and aldehydes is shown to give α-alkoxyl-β- hydroxyl acid derivatives; the novel C-C bond formation reaction is proposed to occur through oxonium ylides derived from diazo compounds and titanium alkoxides, and followed by intermolecular trapping by aldehydes. The Royal Society of Chemistry 2005.
Gold(I)-catalyzed diazo coupling: Strategy towards alkene formation and tandem benzannulation
Zhang, Daming,Xu, Guangyang,Ding, Dong,Zhu, Chenghao,Li, Jian,Sun, Jiangtao
, p. 11070 - 11074 (2015)
A gold(I)-catalyzed cross-coupling of diazo compounds to afford tetrasubstituted alkenes has been developed by taking advantage of a trivial electronic difference between two diazo substrates. A N-heterocyclic-carbene-derived gold complex is the most effective catalyst for this transformation. Based on this new strategy a gold(I)-initiated benzannulation has been achieved through a tandem reaction involving a diazo cross-coupling 6πelectrocyclization and oxidative aromatization.
Reductive homo-coupling of methyl 2-Br-2-Cl-carboxylates promoted by CuBr-Fe0
Benincasa, Marta,Forti, Luca,Ghelfi, Franco,Pagnoni, Ugo M.
, p. 1103 - 1106 (1995)
Dimethyl 2,3-dialkyl-2,3-dichloro-butanedioates are efficiently prepared in dimethylformamide or dimethylsulphoxide, through reductive homo-coupling of methyl 2-bromo-2-chlorocarboxylates promoted by CuBr-Fe0.
Stereoselective Synthesis of Tetrasubstituted Furylalkenes via Gold-Catalyzed Cross-Coupling of Enynones with Diazo Compounds
Liu, Pei,Sun, Jiangtao
, p. 3482 - 3485 (2017)
A stereoselective, gold-catalyzed, cross-coupling reaction of enynones with diazo compounds has been developed, affording 2-alkenylfurans in moderate to good yields with excellent E-stereoselectivity. Upon using diazo compounds as nucleophiles to trap the in situ formed gold furyl carbene, this protocol provides a novel path toward the formation of unsymmetrical tetrasubstituted alkenes.
Selective Vinylogous Reactivity of Carbene Intermediate in Gold-Catalyzed Alkyne Carbocyclization: Synthesis of Indenols
Zhang, Cheng,Li, Hongli,Pei, Chao,Qiu, Lihua,Hu, Wenhao,Bao, Xiaoguang,Xu, Xinfang
, p. 2440 - 2447 (2019)
A gold-catalyzed carbocyclization of alkynes with a pendant diazo group that is completed by reaction with a protic nucleophile for the synthesis of indenol derivatives with a tertiary center is described. Mechanistic studies and DFT calculations indicate
110. Synthesis of 1H-Cyclopropanaphthalenes via Trapping of o-Benzoquinodimethanes
Mueller, Paul,Rodriguez, Domingo
, p. 975 - 980 (1985)
1H-Cyclopropanaphthalene (10a) and 3-methyl or dimethyl derivatives have been synthesized by interception of appropriately substituted o-quinodimethanes 3 with 1-bromo-2-chlorocyclopropene 5, and subsequent dehydrohalogenation of the adducts.The o-quin
Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction
Li, Ziyong,Sun, Jiangtao
, p. 3706 - 3711 (2021)
A copper-catalyzed three-component reaction of terminal alkynes, diazo compounds, and B2pin2 to prepare trisubstituted alkenylboronates has been developed. This difunctionalization of alkynes selectively occurs at the terminal carbon atom and proceeds via
Blue Light-Promoted Formal [4+1]-Annulation of Diazoacetates with o-Aminoacetophenones: Synthesis of Polysubstituted Indolines and Computational Study
Chen, Jinzhou,Liu, Shuhao,Lv, Xinxin,Hong, Kemiao,Lei, Jinping,Xu, Xinfang,Hu, Wenhao
, p. 13920 - 13928 (2020)
A blue light-promoted formal [4+1]-annulation of diazoacetates with o-aminoacetophenones has been reported, which provides an environmentally friendly method for the synthesis of polysubstituted indoline derivatives in moderate to good yields with excellent diastereoselectivities. Detailed mechanistic studies through density functional theory calculations reveal that the (E)-enol species is the key intermediate in this transformation, and the excellent diastereoselectivity is enabled via H-bonding in the intramolecular Aldol-type addition.
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.
A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides
Yu, Sifan,Chen, Jinzhou,Liu, Gengxin,Lei, Jinping,Hu, Wenhao,Qiu, Huang
supporting information, p. 1649 - 1652 (2020/02/18)
Gold(i) catalysts are considered to be efficient in promoting sp2 C-H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a
