Chemistry - An Asian Journal
Chemistry - An Asian Journal
4 years ago

Cobalt-Catalyzed Cross-Dehydrogenative C(sp2)−C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane

Cobalt-Catalyzed Cross-Dehydrogenative C(sp2)−C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane
Xiaojiao Wang, Ziyuan Li, Hao Zuo, Xinyue Zhang, Lisi Zhu, Bowen Lei, Dailin Zhuang, Lifang Ma
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. Direct C5-alkylation of oxazole/thiazole with ether or cycloalkane through a cobalt-catalyzed cross-dehydrogenative coupling (CDC) process is reported. This transformation represents the first C(sp2)−C(sp3) cross-coupling at the C5-position of the azole via double C−H bond cleavages. A preliminary mechanism involving a radical process has also been proposed.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201701258

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