One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation

被引:137
作者
Jayakumar, Jayachandran [1 ]
Parthasarathy, Kanniyappan [1 ]
Chen, Yi-Hsiang [1 ]
Lee, Tai-Hua [2 ]
Chuang, Shih-Ching [2 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
[2] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30013, Taiwan
关键词
alkynes; annulation; benzamidines; CH activation; rhodium; CATALYZED OXIDATIVE COUPLING/CYCLIZATION; N BOND FORMATION; INTERNAL ALKYNES; ISOQUINOLONE SYNTHESIS; COUPLING REACTIONS; RHODIUM CATALYSIS; DIRECTING GROUP; BENZOIC-ACIDS; ARYL KETONES; O BOND;
D O I
10.1002/anie.201405183
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the synthesis of highly substituted naphthyridine-based polyheteroaromatic compounds in high yields proceeds through rhodium(III)-catalyzed multiple CH bond cleavage and CC and CN bond formation in a one-pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique -conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation-assisted ortho CH activation, alkyne insertion, and reductive elimination, is proposed for this transformation.
引用
收藏
页码:9889 / 9892
页数:4
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