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Short Paper | Regular issue | Vol 92, No. 9, 2016, pp.1687-1697
Published online, 15th July, 2016
DOI: 10.3987/COM-16-13506
Lewis Acid-Catalyzed Borono-Minisci Reactions of Arylboronic Acids and Heterocycles

Joyce L. Biaco, Savannah L. Jones, and Timothy J. Barker*

*Department of Chemistry and Biochemistry, College of Charleston, 66 George St., Charleston, SC 29424, U.S.A.

Abstract

A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Brønsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.