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Updated: Feb 22, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Cobalt-Catalyzed Cross-Dehydrogenative C(sp2 )-C(sp3 ) Coupling of Oxazole/Thiazole with Ether or Cycloalkane
Xiaojiao Wang1, Bowen Lei1, Lifang Ma1
1Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, No.24 South Section 1, Yihuan Road, Chengdu, 610065, China.
Abstract:
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(sp2 )-C(sp3 ) 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. A preliminary mechanism involving a radical process has also been proposed.
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