Work

Practical C−H Functionalization of Quinones with Boronic Acids

Year: 2011

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja111152z

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

Institution: Scripps Research Institute

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Synthesis of Pyrrole-Imidazole Alkaloids, G963544812