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

Practical C-H functionalization of quinones with boronic acids

Yuta Fujiwara  1 , Victoriano Domingo, Ian B Seiple, Ryan Gianatassio, Matthew Del Bel, Phil S Baran
Affiliations

Practical C-H functionalization of quinones with boronic acids

Yuta Fujiwara et al. J Am Chem Soc. .

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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Figures

Figure 1
Figure 1
(A) Traditional access to functionalized quinones. (B) Initial findings with respect to arylboronic acid reactivity.
Figure 2
Figure 2
Exploration of Molander salts and purely aqueous conditions.
Figure 3
Figure 3
Applications to natural products and natural product hybrids.
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