Hydrogenation of indole by phosphine-modified rhodium and ruthenium catalysts

被引：35

作者：

Barbaro, P ^{[1
]}

Bianchini, C ^{[1
]}

Meli, A ^{[1
]}

Moreno, M ^{[1
]}

Vizza, F ^{[1
]}

机构：

[1] CNR, ISSECC, I-50132 Florence, Italy

来源：

ORGANOMETALLICS | 2002年 / 21卷 / 07期

关键词：

D O I：

10.1021/om011005n

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The selective hydrogenation of indole (IN) to indoline (INE) by rhodium and ruthenium catalysts modified with the tripodal polyphosphine ligand MeC(CH(2)PPh(2))(3) (triphos) has been investigated in the homogeneous phase. Both [Rh(DMAD)(triphos)]PF(6) (DMAD = dimethyl acetylenedicarboxylate) and [Ru(MeCN)(3)(triphos)](SO(3)CF(3))(2) have been found to generate effective catalysts for the conversion of IN to INE in THF in the presence of triflic acid. The protic acid is required to generate the 3H-indolium cation, which contains a localized C=N bond. The rhodium precursor was more efficient than the ruthenium species and allowed for hydrogenation of the substrate even at 60 degreesC with turnover frequencies as high as 100. Catalytic experiments in autoclaves and in high-pressure sapphire NMR tubes have provided valuable information on the hydrogenation mechanism of IN.

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页码：1430 / 1437

页数：8

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