Iridium-Catalyzed C-H Borylation of Cyclopropanes

Carl W. Liskey and John F. Hartwig*

*University of California, Berkeley, California 94720, United States, Email: jhartwigberkeley.edu

C. W. Liskey, J. F. Hartwig, J. Am. Chem. Soc., 2013, 135, 3375-3378.

DOI: 10.1021/ja400103p

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Abstract

(η⁶-mes)IrBpin₃ or [Ir(COD)OMe]₂ catalyzes the borylation of cyclopropanes in the presence of the phenanthroline derivative 2,9-Me₂phenanthroline as ligand. The borylation occurs selectively at the methylene C-H bonds of the cyclopropane ring in high diasteroselectivities. The cyclopropylboronate esters can be converted to trifluoroborate salts, boronic acids, cyclopropylarenes, cyclopropylamines, and cyclopropanols.

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Key Words

alkylboronates

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ID: J48-Y2013-0560