Practical C-H functionalization of quinones with boronic acids.

doi:10.1021/ja111152z

Paper

Practical C-H functionalization of quinones with boronic acids.

Published Feb 22, 2011 · Yuta Fujiwara, V. Domingo, I. Seiple

Journal of the American Chemical Society

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275

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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 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.

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Study Snapshot

Direct functionalization of quinones with boronic acids is a scalable, room-temperature reaction using inexpensive reagents, with potential applications in complex substrates like steroid derivatives and farnesyl natural products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Practical C-H functionalization of quinones with boronic acids.

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