1326704-90-8Relevant articles and documents
Accelerated photocatalytic [3+2] cycloaddition of phenols and olefins in nESI-MS
Na, Na,Ouyang, Jin,Sun, Jianghui,Wei, Juanjuan,Yin, Yiyan,Zeng, Ni
, (2021/11/22)
The photocatalytic [3+2] cycloadditions of phenols and olefins are normally limited by the relatively tedious process. Herein, based on accelerated microdroplet reactions, a nano-electrospray ionization (nESI) was constructed for online acceleration of photocatalytic [3+2] cycloaddition between phenols and olefins. As demonstrated, the high reaction rates were obtained by nESI tips with smaller orifice inner diameter and the electrode closed to the nESI tip. These were further confirmed by the calculations on the conversion ratios and apparent acceleration factors. Meanwhile, the important intermediates (especially short-lived radicals) were recorded by virtue of the online monitoring of nESI mass spectrometry (MS). Subsequently, the dynamic information of substrates, intermediates and products were examined. Therefore, the mechanism of photocatalytic [3+2] cycloaddition reactions between phenols and olefins was proposed. This work not only enlarges the application of microdroplet synthesis, but also would provide a possible perspective for accelerating photocatalytic reactions and mechanism examinations.
Metal-Free [3+2] Oxidative Coupling of Phenols with Alkenes: Synthesis of Dihydrobenzofurans
Zhao, Yating,Huang, Binbin,Yang, Chao,Li, Bing,Xia, Wujiong
, p. 2731 - 2737 (2015/09/15)
Herein, we demonstrated a benign and metal-free [3+2]-cycloaddition reaction using simple and readily available phenols and styrenes as substrates and sodium persulfate as an inexpensive and environmentally friendly oxidant for the direct synthesis of dih
[3 + 2] coupling of quinone monoacetals by combined acid-hydrogen bond donor
Dohi, Toshifumi,Hu, Yinjun,Kamitanaka, Tohru,Washimi, Naohiko,Kita, Yasuyuki
, p. 4814 - 4817 (2011/11/13)
The expeditious and efficient [3 + 2] coupling approach of quinone monoacetals 1 with alkene nucleophiles 2 by the action of an activated Bronsted acid in the presence of a hydrogen bond donor perfluorinated alcohol has been achieved. With the optimized combined acid, the reaction could proceed under mild conditions by only mixing the two reactants to afford the cycloadducts 3 in a short time (within 10 min) with good to quantitative yields.