Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 18, Pages 2884-2898Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900032
Keywords
Heterocycles; Oxazole; Bromination; Regioselectivity; Suzuki coupling
Categories
Funding
- Enamine Ltd.
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An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki-Miyaura cross-coupling reaction under parallel synthesis conditions.
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