10420-73-2Relevant articles and documents
Palladium-catalyzed carbonylation reaction of aryl bromides with 2-hydroxyacetophenones to form flavones
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
, p. 12595 - 12598 (2012)
Flavone of the month: A general and efficient method for the palladium-catalyzed carbonylative synthesis of flavones has been developed (see scheme). Starting from aryl bromides and 2-hydroxyacetophenones, the corresponding flavones have been isolated in good yields. Copyright
Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes
Yue, Yixia,Peng, Jinsong,Wang, Deqiang,Bian, Yunyun,Sun, Peng,Chen, Chunxia
, p. 5481 - 5486 (2017)
The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.
CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones
Sun, Dong-Wei,Zhou, Yong-Yan,Jiang, Min,Nian, Tang,Liu, Jin-Tao
, (2021)
An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.
An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation
Agisho, Habtamu Abebe,Hairat, Suboot,Zaki, Mehvash
, p. 599 - 603 (2020)
Abstract: A transition metal-free and efficient TBHP/TBAI-mediated protocol has been developed for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. It proceeds in the presence of a catalytic amount of tetrabutylammonium iodide and oxidant tert-butyl hydroperoxide (TBHP, 5–6 M in decane) to afford the corresponding products in good to excellent yields. Furthermore, it has been observed that an increase in the concentration of TBHP to 30 mol % drastically increases the yield of 4H-chromen-4-ones, any further increase will lead to a decrease in percent yield. The mechanism of this reaction involves the generation of tertiary butoxide radical initially which by oxidative single-electron transformation is converted to iodochroman-4-one. Later the hydrogen iodide is removed from iodochroman-4-one to give the desired product, i.e. 4H-chromen-4-ones. Moreover, this is a rare example of the n-Bu4NI/TBHP-mediated C–C bond through dehydrogenative reaction. Graphic abstract: [Figure not available: see fulltext.]
Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
Cheng, Kang,Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
, p. 392 - 398 (2019)
Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.
Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions
Unde, Pradip J.,Thorat, Nitin M.,Patil, Limbraj R.
, p. 1133 - 1136 (2019)
A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.