Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 11, Pages 4272-4277Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900513z
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Funding
- Japan Society for the Promotion of Science (JSPS) [19890179]
- Japan Science and Technology Agency (JST) [08-119]
- The Saijiro Endo Memorial Foundation for Science Technology
- Grants-in-Aid for Scientific Research [19890179, 21390033] Funding Source: KAKEN
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An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.
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