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Practical C-H functionalization of quinones with boronic acids.

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.

SUBMITTER: Fujiwara Y

PROVIDER: S-EPMC3964812 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Practical C-H functionalization of quinones with boronic acids.

Fujiwara Yuta Y Domingo Victoriano V Seiple Ian B IB Gianatassio Ryan R Del Bel Matthew M Baran Phil S PS

Journal of the American Chemical Society 20110222 10

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 wit ...[more]

PMID: 21341741

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