Title |
Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles
|
---|---|
Published in |
Journal of Organic Chemistry, March 2018
|
DOI | 10.1021/acs.joc.7b03100 |
Pubmed ID | |
Authors |
Joseph Derosa, Miriam L. O’Duill, Matthew Holcomb, Mark N. Boulous, Ryan L. Patman, Fen Wang, Michelle Tran-Dubé, Indrawan McAlpine, Keary M. Engle |
Abstract |
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 cyclopropylation reaction using potassium cyclopropyl trifluoroborate 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-cyclopropylation. The transformation is catalyzed by Cu(OAc)2 and 1,10-phenanthroline and employs 1 atm O2 as the terminal oxidant. This method is operationally convenient to perform and provides a simple, strategic disconnection toward the synthesis of cyclopropyl aryl ethers and cyclopropyl amine derivatives bearing an array of functional groups. |
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Luxembourg | 1 | 7% |
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Mexico | 1 | 7% |
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Scientists | 7 | 47% |
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Researcher | 11 | 19% |
Student > Ph. D. Student | 9 | 15% |
Student > Doctoral Student | 3 | 5% |
Other | 3 | 5% |
Other | 11 | 19% |
Unknown | 11 | 19% |
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Biochemistry, Genetics and Molecular Biology | 3 | 5% |
Chemical Engineering | 1 | 2% |
Medicine and Dentistry | 1 | 2% |
Unknown | 10 | 17% |