1036579-09-5Relevant 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.
Towards aryl C-N bond formation in dynamic thin films
Gandy, Michael N.,Raston, Colin L.,Stubbs, Keith A.
supporting information, p. 4594 - 4597 (2014/06/24)
C-N bond forming reactions are important in organic chemistry. A thin film microfluidic vortex fluidic device (VFD) operating under confined mode affords N-aryl compounds from 2-chloropyrazine and the corresponding amine, without the need for a transition
