223690-04-8Relevant articles and documents
Copper-catalyzed chan-lam cyclopropylation of phenols and azaheterocycles
Derosa, Joseph,O'Duill, Miriam L.,Holcomb, Matthew,Boulous, Mark N.,Patman, Ryan L.,Wang, Fen,Tran-Dubé, Michelle,McAlpine, Indrawan,Engle, Keary M.
, p. 3417 - 3425 (2018/04/14)
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 of 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.
A convenient method for the preparation of aryl cyclopropyl ethers from phenols
Hollingworth, Gregory J.,Dinnell, Kevin,Dickinson, Laura C.,Elliott, Jason M.,Kulagowski, Janusz J.,Swain, Christopher J.,Thomson, Christopher G.
, p. 2633 - 2636 (2007/10/03)
A general method for the synthesis of cyclopropyl ethers from phenols is described. Alkylation of a phenol using 1-iodo-1-(phenylthio)cyclopropane followed by removal of the phenylthio group furnishes the cyclopropyl ethers in modest to excellent yields. The procedure tolerates a wide range of functional groups.
