74475-24-4Relevant articles and documents
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.
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.
