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(sp)-C(sp) 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.
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Cobalt-Catalyzed Cross-Dehydrogenative C(sp )-C(sp ) Coupling of Oxazole/Thiazole with Ether or Cycloalkane.
Chem Asian J
November 2017
Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, No.24 South Section 1, Yihuan Road, Chengdu, 610065, China.
Direct C5-alkylation of oxazole/thiazole with ether or cycloalkane has been achieved through a cobalt-catalyzed cross-dehydrogenative coupling (CDC) process in moderate to good yields. This transformation represents the first C(sp )-C(sp ) cross-coupling at the C5-position of the oxazole/thiazole via double C-H bond cleavages. Various functional groups on oxazole/thiazole substrates, as well as water and air, are well-tolerated with this concise and practical protocol, constituting straightforward access to heterocycles with great medicinal significance.
View Article and Find Full Text PDFDDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C-H bond activation.
Org Biomol Chem
July 2017
Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
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(sp)-C(sp) 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.
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