Download PDF
Synthesis 2010(9): 1441-1448  
DOI: 10.1055/s-0029-1218683
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(II)-Catalyzed Conversion of Aryl/Heteroaryl Boronic Acids, Boronates, and Trifluoroborates into the Corresponding Azides: Substrate Scope and Limitations

Kimberly D. Grimes, Amol Gupte, Courtney C. Aldrich*
Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, MN 55455, USA
Fax: +1(612)6265173; e-Mail: aldri015@umn.edu;
Further Information

Publication History

Received 2 November 2009
Publication Date:
24 February 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

We report the copper(II)-catalyzed conversion of organoboron compounds into the corresponding azide derivatives. A systematic series of phenylboronic acid derivatives is evaluated to examine the importance of steric and electronic effects of the substituents on reaction yield as well as functional group compatibility. Heterocyclic substrates are also shown to participate in this mild reaction while compounds incorporating B-C(sp³) bonds are unreactive under the reaction conditions. The copper(II)-catalyzed boronic acid-azide coupling reaction is further extended to both boronate esters and potassium organotrifluoroborate salts. The method described herein complements existing procedures for the preparation of aryl azides from the respective amino, triazene, and halide derivatives and we expect that it will greatly facilitate copper- and ruthenium-catalyzed azide-alkyne cycloaddition reactions for the preparation of diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3-triazoles derivatives.

Key words

azides - organoboron compounds - copper catalysis - 1,2,3-triazoles