Chemical Communications

A novel and direct synthesis of indoles via catalytic reductive annulation of nitroaromatics with alkynes

A Penoni, KM Nicholas

Index: Penoni, Andrea; Nicholas, Kenneth M. Chemical Communications, 2002 , # 5 p. 484 - 485

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Citation Number: 25

Abstract

In our initial experiments 1-phenylpropyne and nitrobenzene were heated together with [CpFe(CO) 2 ] 2 (1a) under CO pressure (dioxane, 170 °C, 750 psi, 24 h); GC/MS monitoring indicated the formation of a major product (ca. 20%) with the mass of the expected amine (m/e 207) as well as lesser quantities of aniline (12%), azo- (15%) and azoxybenzene (8%). Isolation of this material in fact showed it to be 2-methyl-3-phenylindole (2a) 9 rather than ...