Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles
Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles
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DOI：
10.1021/jo201795t
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发表时间：
2011-12-16
影响因子：
3.6
通讯作者：
Wu, Ming-Jung
中科院分区：
文献类型：
--
作者：
Chen, Chin-Chau;Yang, Shyh-Chyun;Wu, Ming-Jung
用 1.2 当量碘的 CH2Cl2 溶液处理 N,N-二甲基 2-[2-(2-乙炔基苯基)乙炔基]苯胺 (1)，以良好的收率得到苯并[a]咔唑 (2)。机理研究表明该反应必须经过卤代吲哚 (3)，然后进行碘鎓离子催化的原子转移环化反应，得到苯并[a]咔唑。
Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH2Cl2 gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.