Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters. Issue 46 (16th November 2017)

• Record Type: Journal Article
• Authors: Xu, Xiaohe; Sun, Jian; Lin, Yuyan; Cheng, Jingya; Li, Pingping; Yan, Yiyan; Shuai, Qi; Xie, Yuanyuan
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 46(2017)
• Page Start: 9875
• Page End: 9879
• Publication Date: 2017-11-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02249b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel oxygenative cross dehydrogenative coupling of ethers and alkanes with NHPI under a copper nitrate/oxygen catalytic system is described. Abstract : A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N -hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N -alkoxyphthalimides. In addition, it was found that when tert -butyl ethers were used as substrates, unexpected N -hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.