74475-24-4Relevant academic research and scientific papers
Direct C-H arylation of quinones with anilines
Lamblin, Marc,Naturale, Guillaume,Dessolin, Jean,Felpin, Fran?ois-Xavier
, p. 1621 - 1624 (2012)
We discovered that anilines were suitable for the direct C-H arylation of benzoquinone in the presence of tert-butyl nitrite. This new reaction proceeds through the in situ formation of a diazonium hydroxide species. The coupling can be carried out at room temperature under neutral, additive-free, metal-free, and aqueous conditions, allowing an environmentally friendly procedure. Georg Thieme Verlag Stuttgart · New York.
C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium
Wang, Liang,Shen, Jun,Yang, Sen,Liu, Wenjie,Chen, Qun,He, Mingyang
supporting information, p. 1290 - 1296 (2018/03/26)
A PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for radical C-H arylation reactions. The arylation process involved coupling of in situ generated aryl diazonium salts from aniline with heteroarenes, enol acetates or benzoquinones under visible light in aqueous medium or pure water. A broad range of substrates survived the reaction conditions to provide the desired products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. This semiconductor photocatalyst showed good photocatalytic performance and stability. Recycle studies showed that this composite could be readily recovered and a slight decrease in the catalytic activity was observed after ten consecutive runs.
Practical C-H functionalization of quinones with boronic acids
Fujiwara, Yuta,Domingo, Victoriano,Seiple, Ian B.,Gianatassio, Ryan,Del Bel, Matthew,Baran, Phil S.
supporting information; experimental part, p. 3292 - 3295 (2011/05/03)
A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.
New and efficient protocol for arylation of quinones
Demchuk, Oleg M.,Pietrusiewicz, K. Micha?
scheme or table, p. 1149 - 1153 (2009/10/17)
A practical rhodium-mediated arylation of 1,4-quinones has been developed. The corresponding 2-aryl-1,4-quinones were obtained with excellent selectivity and high yields under convenient aerobic reaction conditions. Georg Thieme Verlag Stuttgart.
