Cu-catalyzed oxygenation of alkene-tethered amides with O2via unactivated C&xe001;C bond cleavage: a direct approach to cyclic imides

被引:31
|
作者
Li, Junhua [1 ]
Wei, Jialiang [1 ]
Zhu, Bencong [1 ]
Wang, Teng [2 ]
Jiao, Ning [1 ,3 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China
[2] Beihang Univ, Sch Chem, Xue Yuan Rd 38, Beijing 100191, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
MOLECULAR-OXYGEN; OXIDATIVE CLEAVAGE; 3-COMPONENT CARBOAZIDATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; AEROBIC CLEAVAGE; METAL-FREE; C=C BONDS; CYCLIZATION; WATER;
D O I
10.1039/c9sc03175h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The transformations of unactivated alkenes through C & xe001;C bond double cleavage are always attractive but very challenging. We report herein a chemoselective approach to valuable cyclic imides by a novel Cu-catalyzed geminal amino-oxygenation of unactivated C & xe001;C bonds. O-2 was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via C & xe001;C bond cleavage for the efficient preparation of succinimide or glutarimide derivatives. Moreover, the present strategy under simple conditions can be used in the late-stage modification of biologically active compounds and the synthesis of pharmaceuticals, which demonstrated the potential application.
引用
收藏
页码:9099 / 9103
页数:5
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