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J Am Chem Soc. 2011 Mar 16;133(10):3292-5. doi: 10.1021/ja111152z. Epub 2011 Feb 22.

Practical C-H functionalization of quinones with boronic acids.

Author information

1
Department of Chemistry and Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

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.

PMID:
21341741
PMCID:
PMC3964812
DOI:
10.1021/ja111152z
[Indexed for MEDLINE]
Free PMC Article

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