钯（II）催化烯二炔环化合成苯并[a]咔唑及其机理研究。
Synthetic development and mechanistic study on Pd(II)-catalyzed cyclization of enediynes to benzo[a]carbazoles.
机构信息
School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.
出版信息
Org Lett. 2010 Dec 17;12(24):5652-5. doi: 10.1021/ol1024458. Epub 2010 Nov 18.
PMID:21087056
Abstract
Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol % of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.
摘要
用 10 mol%的氯化钯和 2 当量的氯化铜处理 N,N-二甲基 2-[2-(2-乙炔基苯基)乙炔基]苯胺（1），在回流的四氢呋喃中得到苯并[a]咔唑（6），产率良好。一项机理研究表明，该反应必须经过卤吲哚（7）的形成，然后进行钯（II）催化的原子转移环化反应，才能得到苯并[a]咔唑。
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