We report the efficient synthesis of alkyl ethers by the functionalization of unactivated sp 3- and sp 2-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(sp 3)-H bond of methyl groups, as functional groups in organic synthesis.
|Original language||English (US)|
|Number of pages||4|
|Journal||Journal of the American Chemical Society|
|State||Published - May 2 2012|
All Science Journal Classification (ASJC) codes
- Colloid and Surface Chemistry