Gold(I)-Catalyzed Polycyclizations of Polyenyne-Type Anilines Based on Hydroamination and Consecutive Hydroarylation Cascade

被引：84

作者：

Hirano, Kimio ^{[1
]}

Inaba, Yusuke ^{[1
]}

Takasu, Kiyosei ^{[1
]}

Oishi, Shinya ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroald ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 21期

关键词：

RUTHENIUM-CATALYZED AROMATIZATION; HOMOGENEOUS GOLD CATALYSIS; ENEDIYNE MODEL COMPOUNDS; C-H BONDS; ANIONIC CYCLOAROMATIZATION; INTERMOLECULAR REACTIONS; NUCLEOPHILIC ADDITIONS; CYCLIZATION; ALKYNES; CYCLOISOMERIZATION;

D O I：

10.1021/jo2018119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A hydroamination-double hydroarylation cascade using aniline derivatives bearing a trienyne moiety as the substrate was efficiently promoted by a gold(I) catalyst to produce benzo[a]naphtho [2,1-c]carbazole derivatives in good yields. This reaction is applicable to various substituted trienyne-type anilines, including 2,3-diethynylthiophene derivatives. The reaction of anilines bearing a tetraenyne and pentaenyne moiety allows direct construction of highly fused carbazoles by tetra- and pentacyclization, respectively, through hydroamination and consecutive hydroarylation without producing any theoretical waste products from the substrates.

引用

页码：9068 / 9080

页数：13

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