Palladium-catalyzed Csp2–H carbonylation of aromatic oximes: selective access to benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones?

Chemical Communications Pub Date: 2015-03-11 DOI: 10.1039/C5CC01661D

Abstract

A highly selective palladium-catalyzed carbonylation of Csp2–H bonds with aromatic oximes for the synthesis of benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones has been developed. Interestingly, we found that the N–OH group of the oximes could be used as a directing group and/or an internal oxidant under different conditions. This transformation is supposed to proceed through a hydroxyl-directed ortho-Csp2–H carbonylation or activation of vinyl Csp2–H bond/ortho-Csp2–H carbonylation process. The uses of readily available starting materials, atmospheric pressure of carbon monoxide, as well as operational simplicity make this practical and atom-economical method particularly attractive.

Graphical abstract: Palladium-catalyzed Csp2–H carbonylation of aromatic oximes: selective access to benzo[d][1,2]oxazin-1-ones and 3-methyleneisoindolin-1-ones
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