Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines

被引:69
|
作者
Zhu, Zhongzhi [1 ]
Tang, Xiaodong [1 ]
Li, Xianwei [1 ]
Wu, Wanqing [1 ]
Deng, Guohua [1 ]
Jiang, Huanfeng [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 04期
基金
中国国家自然科学基金;
关键词
VINYL AZIDES; GAMMA-LACTONES; CROSS-COUPLING/CYCLIZATION; SUBSTITUTED ISOQUINOLINES; EFFICIENT SYNTHESIS; IRIDIUM COMPLEXES; INTERNAL ALKYNES; BOND ACTIVATION; COPPER; ANNULATION;
D O I
10.1021/acs.joc.5b02376
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and N-15 isotope labeling experiments were conducted for the mechanistic research.
引用
收藏
页码:1401 / 1409
页数:9
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