54945-17-4Relevant articles and documents
1-butyl-3-methylimidazol-2-ylidene as an efficient catalyst for cross-coupling between aromatic aldehydes and N-aroylbenzotriazoles
Phungpis, Baramee,Hahnvajanawong, Viwat
, p. 651 - 657 (2021/02/27)
Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.
Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation
Mei, Xiaochuan,Hu, Weican,Gao, Kexin,Gao, Haotian,Wang, Chaoyang,Qian, Guoying,Rong, Zhouting
supporting information, p. 2661 - 2667 (2021/07/09)
The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.
Ruthenium/dendrimer complex immobilized on silica-functionalized magnetite nanoparticles catalyzed oxidation of stilbenes to benzil derivatives at room temperature
Ghanaatzadeh, Niloofar,Hashemi, Hajar,Moghadam, Majid,Niknam, Khodabakhsh,Saberi, Dariush
, (2020/02/13)
A new ruthenium/dendrimer complex stabilized on the surface of silica-functionalized nano-magnetite was fabricated and well characterized. The nano-catalyst showed good activity in the synthesis of benzil derivatives via the oxidation of stilbenes with high turnover frequency (TOF) at room temperature. Moreover, the catalyst could also be reused up to fifteen times without any loss of its activity.
Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature
Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Sagadevan, Arunachalam
supporting information, p. 4426 - 4432 (2020/08/10)
We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ～2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is
Selective oxygenation of alkynes: A direct approach to diketones and vinyl acetate
Xia, Xiao-Feng,Gu, Zhen,Liu, Wentao,Wang, Ningning,Wang, Haijun,Xia, Yongmei,Gao, Haiyan,Liu, Xiang
supporting information, p. 9909 - 9913 (2015/01/09)
Arylalkynes can be converted into α-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)2 as an oxidant at room temperature. A series of substituted α-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes. This journal is
Copper-mediated aerobic oxidative cleavage of α,β-unsaturated ketones to 1,2-diketones
Li, Zheng,Yin, Junjun,Wen, Gong,Li, Tianpeng,Shen, Xiaoli
, p. 32298 - 32302 (2014/08/18)
The copper-mediated aerobic oxidative cleavage of α,β- unsaturated ketones to synthesize 1,2-diketones by using potassium acetate as a catalyst and sodium iodide as a promoter in acetic acid is described. The protocol has the advantages of using inexpensive and non-toxic raw materials, high yield and simple work-up procedure. the Partner Organisations 2014.
Copper-catalyzed oxidation of deoxybenzoins to benzils under aerobic conditions
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia,Verdiglione, Rosanna
supporting information, p. 1701 - 1707 (2013/07/27)
A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the oxidant has been developed. The reaction tolerates a variety of useful substituents including chloro, bromo, iodo, keto, ester, and cyano groups. Georg Thieme Verlag Stuttgart, New York.
One-pot synthesis of unsymmetrical benzils and N-heteroarenes through nucleophilic aroylation catalyzed by N-heterocyclic carbene
Suzuki, Yumiko,Murofushi, Mai,Manabe, Kei
, p. 470 - 473 (2013/02/25)
An efficient one-pot synthesis of various unsymmetrical benzils via N-heterocyclic carbene (NHC)-catalyzed aroylation of N-phenylimidoyl chlorides with aromatic aldehydes followed by acidic hydrolysis has been developed. The one-pot procedure was extended to synthesis of quinoxalines and pyrazines by condensation/annulation of unsymmetrical benzils generated in situ with diamines.
Synthesis of unsymmetrical benzils using N-heterocyclic carbene catalysis
Suzuki, Yumiko,Bakar, Abu,Tanoi, Takashi,Nomura, Naoko,Sato, Masayuki
, p. 4710 - 4715 (2011/06/27)
In this paper, we propose a novel and efficient method for the preparation of various unsymmetrical benzils. We first demonstrate the nucleophilic aroylation of N-phenylbenzimidoyl chlorides with aromatic aldehydes using N-heterocyclic carbene as the catalyst to afford 1-aryl-2-phenyl-2-(phenylimino) ethanones. These iminoethanones were then converted to 1,2-diaryl-1,2-diketones by acid-promoted hydrolysis.
Imidoylstannanes, Improved Preparation and Uses as Acylanion Equivalents
Jousseaume, Bernard,Vilcot, Nathalie,Ricci, Alfredo,Tiekink, Edward R. T.
, p. 2283 - 2288 (2007/10/02)
An improved preparation of imidoylstannanes, by reaction of triorganostannyllithiums with imidoyl chlorides, is reported.This reaction is effective when phenyl or methyl groups are substituents on the tin atom, and when N-aryl C-alkyl or C-aryl imidoyl chlorides are used.After reaction with acyl chlorides, imidoylstannanes led to high yields of α-keto imines, which can be further hydrolysed into α-diketones.Transmetallation with organolithiums selectively gave the corresponding lithium reagents which showed a normal behaviour with alkyl halides, silicon halides, epoxides or chloroformates, leading to functional imines, hydrolysable to the corresponding ketones.This route forms a new entry to Walborski reagents.
