Peer-Reviewed Journal Details
Mandatory Fields
Derosa, J;O'Duill, ML;Holcomb, M;Boulous, MN;Patman, RL;Wang, F;Tran-Dube, M;McAlpine, I;Engle, KM
2018
April
Journal Of Organic Chemistry
Copper-Catalyzed Chan-Lam Cyclopropylation of Phenols and Azaheterocycles
Published
Altmetric: 22WOS: 7 ()
Optional Fields
DIRECT N-CYCLOPROPYLATION MEDICINAL CHEMISTRY ARYLBORONIC ESTERS CUPRIC ACETATE CYCLIC AMIDES ACIDS EFFICIENCY REAGENTS CYCLOPROPANOL DISSOCIATION
83
3417
3425
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.
0022-3263
10.1021/acs.joc.7b03100
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