101789-39-3Relevant articles and documents
Copper-catalyzed direct synthesis of diaryl 1,2-diketones from Aryl iodides and propiolic acids
Min, Hongkeun,Palani, Thiruvengadam,Park, Kyungho,Hwang, Jinil,Lee, Sunwoo
, p. 6279 - 6285 (2014)
Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140°C for 6 h in the presence of 10 mol % CuI/Cu(OTf)2 and Cs2CO3, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts.
Design and synthesis of functionalized coordination polymers as recyclable heterogeneous photocatalysts
Ye, Cai-Ping,Xu, Gan,Wang, Zheng,Han, Jie,Xue, Lian,Cao, Fu-Yu,Zhang, Qi,Yang, Lin-Feng,Lin, Li-Zhou,Chen, Xu-Dong
, p. 6470 - 6478 (2018)
The functionalized ligand 9,10-anthraquinone-1,4-dicarboxylate acid (H2AQDC) was designed and synthesized in order to develop metal-organic coordination polymers as heterogeneous catalysts with a photosensitizing feature. Two major considerations of the ligand design are anthraquinone moieties for photosensitizing to harvest light and carboxylate groups for polymeric coordination toward less solubility. A series of transition metal complexes based on this ligand were synthesized subsequently, namely {Co(AQDC)(H2O)3·2H2O}n (Co-AQDC), {Ni(AQDC)(H2O)3·2H2O}n (Ni-AQDC), {[Cu(AQDC)(H2O)3][Cu(AQDC)(H2O)2(DMF)]·(H2O)4}n (Cu-AQDC), {Zn1.5(AQDC)(OH)(H2O)2·H2O}n (Zn-AQDC), {Ag2(AQDC)(CH3OH)}n (Ag-AQDC). Both the ligand and its transition metal complexes are able to catalyze the visible-light driven oxidation reactions of alkynes into 1,2-diketones in air under mild conditions, in which compound Ni-AQDC demonstrates the best activity. This catalyst can be easily isolated from the reaction mixture by filtration with a trace amount of loss in solution and is ready for recycled use after simple washing and drying without any need for regeneration. Remarkably, the catalyst shows no loss of activity after five catalytic cycles and X-ray powder diffraction proves no change in the structure after five runs. This designed metal-organic coordination polymer represents an environmentally friendly, economical and recyclable photocatalyst, constituting a good candidate for photocatalytic organic syntheses in terms of green chemistry.
C-H oxidation using graphite oxide
Jia, Hong-Peng,Dreyer, Daniel R.,Bielawski, Christopher W.
, p. 4431 - 4434 (2011)
Graphite oxide was found to be an effective oxidant for use in a broad range of reactions, including the oxidation of olefins to their respective diones, methyl benzenes to their respective aldehydes, diarylmethanes to their respective ketones, and various dehydrogenations. The temperatures used in the reactions were typically mild (100-120 °C), and the heterogeneous nature of the oxidant facilitated isolation and purification of the desired products. In most cases, no by-products were observed and the desired products were isolated in good to excellent yields.
Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls
Hu, Ming,Li, Jin-Heng,Li, Yang,Lu, Yuan,Luo, Mu-Jia
supporting information, (2020/05/01)
A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).
Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions
Zhou, Jie,Tao, Xiang-Zhang,Dai, Jian-Jun,Li, Chen-Guang,Xu, Jun,Xu, Hong-Mei,Xu, Hua-Jian
supporting information, p. 9208 - 9211 (2019/08/07)
We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.
