Abstract
The oxidative three-component Passerini reaction us ing primary alcohols as aldehyde surrogates with ferric nitrate (Fe(NO 3)3.9H 2O) and TEMPO as the catalyst system under air is described, The reaction has broad scope over all three compone nts.
Highlights
Since Liu and Ma have reported the Fe(NO3)3.9H2O/TEMPO-mediated oxidation of alcohols in DCE at room temperature,[46,47] we considered performing the same reaction in DCE
We have demonstrated that the Fe(NO3)3.9H2O/TEMPO is an effective homogenous catalyst system for oxidative 3C-Passerini reaction using air as oxidant
This work updates the repertoire of catalytic systems for the oxidative 3CPasserini reaction
Summary
Multicomponent reactions (MCR) are attractive because they are generally atom and energy efficient involving multistep procedures in one-pot.[1,2,3,4,5,6,7,8,9] Amongst the MCRs, the isocyanide-based MCRs have been investigated intensively during the past two decades and many novel modifications have been developed which offer products which are building blocks for constructing important heterocyclic and medicinally important scaffolds.[10,11,12,13,14,15,16] Of particular importance in this area is the Passerini three-component (3C) reaction that involves the reaction between an aldehyde or a ketone, an isocyanide and a carboxylic acid to afford an α-acyloxy amide.[17,18,19,20] As a consequence efforts have been directed toward developing alternatives to this important reaction.[21,22,23,24,25,26,27,28,29,30,31,32] in most of the reported 3C-Passerini reactions an aldehyde constitutes the principal starting material which limits the versatility of the reaction. We commenced our investigations of the oxidative 3C-Passerini reaction by treating benzyl alcohol 1a (1.0 equiv) with benzoic acid 2A (1.1 equiv) and tert-butylisocyanide 3a (1.1 equiv) in the presence of Fe(NO3)3.9H2O (10 mol%), TEMPO (10 mol%) in MeCN at room temperature under air.
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