Cobalt‐Catalyzed Cross‐Dehydrogenative C(sp2)−C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane. Issue 21 (13th October 2017)

• Record Type: Journal Article
• Authors: Wang, Xiaojiao; Lei, Bowen; Ma, Lifang; Zhu, Lisi; Zhang, Xinyue; Zuo, Hao; Zhuang, Dailin; Li, Ziyuan
• Is Part Of: Chemistry, an Asian journal. Volume 12:Issue 21(2017)
• Page Start: 2799
• Page End: 2803
• Publication Date: 2017-10-13
• Subjects: C−H bond cleavage -- cross-coupling reactions -- cycloalkylation -- oxazoles -- oxyalkylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201701258
• Languages: English
• ISSNs: 1861-4728

Abstract

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(sp 2 )−C(sp 3 ) 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. Abstract : 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(sp 2 )−C(sp 3 ) 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.