Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 9, Pages 3375-3378Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja400103p
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Funding
- NSF [CHE-1213409]
- Abbott Laboratories
- NSF
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1213409] Funding Source: National Science Foundation
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The borylation of cyclopropanes catalyzed by the combination of (eta(6)-mes)IrBpin(3) or [Ir(COD)-OMe](2) and a phenanthroline derivative is reported. The borylation occurs selectively at the methylene C-H bonds of the cyclopropane ring over methine or methyl C-H bonds. High diasteroselectivities were observed from reactions catalyzed by the combination of iridium and 2,9-Me(2)phenanthroline. The cyclopropylboronate esters that are generated are versatile synthetic intermediates that can be converted to trifluoroborate salts, boronic acids, cyclopropylarenes, cyclopropylamines, and cyclopropanols.
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