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

被引：83

作者：

Chen, Chin-Chau ^{[2
]}

Chin, Lin-Yu ^{[1
]}

Yang, Shyh-Chyun ^{[2
]}

Wu, Ming-Jung ^{[1
]}

机构：

[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 80424, Taiwan

[2] Kaohsiung Med Univ, Sch Pharm, Kaohsiung, Taiwan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 24期

关键词：

1ST TOTAL-SYNTHESIS; PALLADIUM-CATALYZED CYCLIZATION; TRANSITION-METAL-COMPLEXES; ANIONIC CYCLOAROMATIZATION; ANTITUMOR ANTIBIOTICS; ORGANIC-SYNTHESIS; CARBAZOLE; HALOCYCLIZATION; CHEMISTRY; ROUTE;

D O I：

10.1021/ol1024458

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of N,N-dimethyl 2[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol he 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.

引用

页码：5652 / 5655

页数：4

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