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Practical C-H Functionalization of Quinones with Boronic Acids

Yuta Fujiwara, Victoriano Domingo, Ian B. Seiple, Ryan Gianatassio, Matthew Del Bel, and Phil S. Baran*

*Department of Chemistry and Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: pbaranscripps.edu

Y. Fujiwara, V. Domingo, I. B. Seiple, R. Gianatassio, M. Del Bel, P. P. S. Baran, J. Am. Chem. Soc., 2011, 133, 3292-3295.

DOI: 10.1021/ja111152z (free Supporting Information)


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Abstract

A scalable, direct functionalization of various quinones with several boronic acids proceeds readily at room temperature in an open flask using 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.

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Key Words

Cyclic Enones, Arylation, Potassium Peroxydisulfate


ID: J48-Y2011-0500