Palladium on carbon-catalyzed synthesis of 2-and 2,3-substituted indoles under heterogeneous conditions

被引：35

作者：

Monguchi, Yasunari ^{[1
]}

Mori, Shigeki ^{[1
]}

Aoyagi, Satoka ^{[1
]}

Tsutsui, Azusa ^{[1
]}

Maegawa, Tomohiro ^{[1
]}

Sajiki, Hironao ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Organ Chem Lab, Dept Organ & Med Chem, Gifu 5011196, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 14期

关键词：

ONE-POT SYNTHESIS; MIYAURA COUPLING REACTION; LIGAND-FREE; INTERNAL ALKYNES; 2-SUBSTITUTED INDOLES; 2,3-DISUBSTITUTED INDOLES; REGIOSELECTIVE SYNTHESIS; PRACTICAL SYNTHESIS; REACTION SEQUENCE; FACILE SYNTHESIS;

D O I：

10.1039/c004939e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient and LiCl-free synthetic method for indole derivatives based on the heteroannulation of alkynes with 2-iodoanilines was achieved using palladium on carbon (Pd/C) and NaOAc in heated NMP. The N-tosyl protection of 2-iodoaniline expedited the reaction progress, while other protecting groups, such as tert-butoxycarbonyl, acetyl, and benzyloxycarbonyl groups, underwent deprotection under the present conditions. A variety of di- and monosubstituted alkynes could effectively react with N-tosyl-2-iodoaniline to give the corresponding indoles in good to high yields.

引用

页码：3338 / 3342

页数：5

共 64 条

[1] Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline [J].