Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 7, Pages 3417-3425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03100
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Funding
- National Institutes of Health [1R35GM125052]
- The Scripps Research Institute (TSRI)
- Pfizer, Inc.
- NSF [NSF/DGE-1346837]
- DAAD
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Small molecules containing cyclopropane-heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan-Lam cydopropylation reaction using potassium cydopropyl tri-fluoroborate has been developed. With phenol nucleophiles, the reaction effects O-cyclopropylation, whereas with 2-pyridones, 2-hydroxybenzimidazoles, and 2-aminopyridines the reaction brings about N-cydopropylation. The transformation is catalyzed by Cu(OAc)(2) and 1,10-phenanthroline and employs 1 atm of O-2 as the terminal oxidant. This method is operationally convenient to perform and provides a simple, strategic disconnection toward the synthesis of cydopropyl aryl ethers and cydopropyl amine derivatives bearing an array of functional groups.
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