Practical C− H Functionalization of Quinones with Boronic Acids

…, V Domingo, IB Seiple, R Gianatassio…

Index: Fujiwara, Yuta; Domingo, Victoriano; Seiple, Ian B.; Gianatassio, Ryan; Del Bel, Matthew; Baran, Phil S. Journal of the American Chemical Society, 2011 , vol. 133, # 10 p. 3292 - 3295

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Citation Number: 152

Abstract

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 ...