Palladium-catalyzed oxime ether directed regioselective C-H alkoxylation of arenes

ABSTRACT

A palladium-catalyzed highly regioselective ortho-C(sp²)-H alkoxylation of oxime ethers with PhI(OAc)₂ as the oxidant and alcohols as the alkoxylation reagents has been developed. Mono-alkoxylated and acetoxylated products could be selectively obtained via tuning the reaction conditions. A series of oxime ethers were tolerated, affording the corresponding products in moderate to good yields. Both primary and secondary alcohols survived the reaction conditions. Moreover, the directing group can be easily removed, thereby providing a straightforward access to substituted aryl ketones.

GRAPHICAL ABSTRACT

KEYWORDS:

• Acetoxylation
• alkoxylation
• C-H activation
• oxime ethers
• palladium catalysis