Selective Halogenation Using an Aniline Catalyst

被引:89
作者
Samanta, Ramesh C. [1 ]
Yamamoto, Hisashi [1 ]
机构
[1] Chubu Univ, Mol Catalyst Res Ctr, Kasugai, Aichi 4878501, Japan
关键词
aniline catalyst; aromatic compounds; halo-cyclization; heteroaromatic compounds; halogenation; BROMINATION; REAGENT;
D O I
10.1002/chem.201502234
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable catalytic process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.
引用
收藏
页码:11976 / 11979
页数:4
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