Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system:: practical synthesis of functionalized indoles

被引：29

作者：

Akao, A

Sato, K

Nonoyama, N

Mase, T

Yasuda, N

机构：

[1] Banyu Pharmaceut Co Ltd, Okazaki, Aichi 4440858, Japan

[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

D O I：

10.1016/j.tetlet.2005.11.145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO3)(2)(.)6H(2)O, Fe(OAc)(2) or Co(acac)(3). These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：969 / 972

页数：4

共 29 条

[1] The reduction of aromatic nitro compounds to amines with hydrogen and platinum-oxide platinum black as a catalyst. XIV [J].

Adams, R ;

Cohen, FL ;

Rees, OW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1927, 49 :1093-1099

[2] Practical synthesis of a potent indolocarbazole-based, DNA topoisomerase inhibitor [J].

Akao, A ;

Hiraga, S ;

Iida, T ;

Kamatani, A ;

Kawasaki, M ;

Mase, T ;

Nemoto, T ;

Satake, N ;

Weissman, SA ;

Tschaen, DM ;

Rossen, K ;

Petrillo, D ;

Reamer, RA ;

Volante, RP .

TETRAHEDRON, 2001, 57 (43) :8917-8923

[3] HYDROGENATION AND HYDROGENOLYSIS [J].

ARNOLD, MR .

INDUSTRIAL AND ENGINEERING CHEMISTRY, 1956, 48 (09) :1629-1642

[4]

ASHMORE PG, 1969, CATALYSIS INHIBITION

[5]

AUGASTINE RL, 1965, CATALYTIC HYDROGENER

[6]

BATCHO AD, ORG SYNTH COLL, V7, P34

[7]

CLARK RD, 1984, HETEROCYCLES, V22, P195

[8] PLATINUM METAL SULFIDES AS HETEROGENEOUS HYDROGENATION CATALYSTS [J].

DOVELL, FS ;

GREENFIELD, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (12) :2767-+

[9]

FREIFELDER M, 1971, PRACTICAL CATALYTIC

[10]

Gribble G. W, 1994, CONTEMP ORG SYNTH, V1, P1

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