title: 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.
authors.affiliation: Department of Chemistry and Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Fujiwara
authors.forename: Victoriano
authors.initials: V
authors.lastname: Domingo
authors.forename: Ian B
authors.initials: IB
authors.lastname: Seiple
authors.forename: Ryan
authors.initials: R
authors.lastname: Gianatassio
authors.forename: Matthew
authors.initials: M
authors.lastname: Del Bel
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D011809:Quinones / Q000737:chemistry*
chemical_list: D001688:Biological Products; D001897:Boronic Acids; D011809:Quinones