Synthetic Development and Mechanistic Study on Pd(II)-Catalyzed Cyclization of Enediynes to Benzo[a]carbazoles

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• 作者：Chin-Chau Chen ; Lin-Yu Chin ; Shyh-Chyun Yang ; Ming-Jung Wu
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：December 17, 2010
• 年：2010
• 卷：12
• 期：24
• 页码：5652-5655
• 全文大小：265K
• 年卷期：v.12,no.24(December 17, 2010)
• ISSN：1523-7052

文摘

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.