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Issue 5, 2015
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A highly-efficient palladium-catalyzed aminocarbonylation/SNAr approach to dibenzoxazepinones

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Abstract

A convenient procedure for the synthesis of dibenzoxazepinones has been developed. Utilizing the protocol of one-pot palladium-catalyzed aminocarbonylation/aromatic nucleophilic substitution (SNAr) sequence, with 2-aminophenols and 2-bromofluorobenzenes as the substrates, the desired dibenzo[b,e][1,4]oxazepin-11(5H)-ones were prepared in moderate to excellent yields. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable dibenzoxazepinone and its derivatives. Mechanistic studies suggest that aminocarbonylation proceeds prior to SNAr.

Graphical abstract: A highly-efficient palladium-catalyzed aminocarbonylation/SNAr approach to dibenzoxazepinones

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Article information


Submitted
23 Feb 2015
Accepted
15 Mar 2015
First published
18 Mar 2015

Green Chem., 2015,17, 2994-2999
Article type
Paper
Author version available

A highly-efficient palladium-catalyzed aminocarbonylation/SNAr approach to dibenzoxazepinones

C. Shen, H. Neumann and X. Wu, Green Chem., 2015, 17, 2994
DOI: 10.1039/C5GC00427F

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