1373618-71-3Relevant academic research and scientific papers
Efficient alkyl ether synthesis via palladium-catalyzed, picolinamide-directed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds at remote positions
Zhang, Shu-Yu,He, Gang,Zhao, Yingsheng,Wright, Kiwan,Nack, William A.,Chen, Gong
supporting information; experimental part, p. 7313 - 7316 (2012/06/15)
We report the efficient synthesis of alkyl ethers by the functionalization of unactivated sp3- and sp2-hybridized C-H bonds. In the Pd(OAc)2-catalyzed, PhI(OAc)2-mediated reaction system, picolinamide-protected amine substrates undergo facile alkoxylation at the γ or δ positions with a range of alcohols, including t-BuOH, to give alkoxylated products. This method features a relatively broad substrate scope for amines and alcohols, inexpensive reagents, and convenient operating conditions. This method highlights the emerging value of unactivated C-H bonds, particularly the C(sp3)-H bond of methyl groups, as functional groups in organic synthesis.
