Efficient Alkyl Ether Synthesis via Palladium-Catalyzed, Picolinamide-Directed Alkoxylation of Unactivated C(sp3)–H and C(sp2)–H Bonds at Remote Positions
- 19 April 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 134 (17), 7313-7316
- https://doi.org/10.1021/ja3023972
Abstract
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.This publication has 67 references indexed in Scilit:
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