4197-82-4Relevant academic research and scientific papers
Substituent effects in the oxidation of 2-alkyl-1,4-dialkoxybenzenes with ceric ammonium nitrate
Love, Brian E.,Simmons, Alexander L.
, p. 5712 - 5715 (2016/11/29)
Increased steric size of alkyl groups and the presence of coordinating atoms on alkoxy groups have both been found to contribute to decreasing yields of diquinones upon reaction of 2-alkyl-1,4-dialkoxybenzenes with CAN. The overall hydrophilicity of the substrates does not appear to be a significant factor in determining the diquinone yield for these reactions.
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.
