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Issue 29, 2017
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DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation

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Abstract

A novel and concise C5-alkylation of oxazoles using alkylboronic acids as alkyl donors via Pd(II)-catalysed C–H bond activation has been achieved in moderate to good yields with satisfactory functional group tolerance. Instead of commonly used BQ as a key promoter, DDQ was discovered to be a better additive that significantly promoted this alkylation. This efficient and advanced method represents the first C(sp2)–C(sp3) cross-coupling reaction at the C5-position of oxazoles, which is particularly attractive due to its potential applications in the late-stage functionalization of oxazole-containing bioactive molecules.

Graphical abstract: DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation

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Publication details

The article was received on 04 May 2017, accepted on 01 Jul 2017 and first published on 03 Jul 2017


Article type: Communication
DOI: 10.1039/C7OB01083D
Citation: Org. Biomol. Chem., 2017,15, 6084-6088
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    DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation

    B. Lei, X. Wang, L. Ma, H. Jiao, L. Zhu and Z. Li, Org. Biomol. Chem., 2017, 15, 6084
    DOI: 10.1039/C7OB01083D

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