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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 24
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Original Articles

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

, , &
Pages 1981-1988 | Received 20 Jul 2016, Published online: 17 Nov 2016
 

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

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