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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 17
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Original Articles

Mild and Efficient PtO2-Catalyzed One-Pot Reductive Mono-N-alkylation of Nitroarenes

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Pages 2490-2502 | Received 04 Oct 2010, Published online: 29 May 2012
 

Abstract

A mild and efficient one-pot reductive monoalkylation of nitroarenes has been described using aldehydes as alkylating agents, molecular hydrogen as a reducing agent, and PtO2 as a catalyst in methanol. This methodology is found to be applicable for both aliphatic and aromatic aldehydes and for a wide variety of nitroarenes.

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GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

V. S. R. thanks the University Grant Commission (UGC), New Delhi, for the award of a junior research fellowship.

Notes

a Reaction conditions: aldehyde (1.5 mmol), nitrobenzene (1 mmol), solvent (5 ml), and PtO2 (8 mol%) at room temperature.

b The times given correspond to the following reactions: reduction of nitroarenes + imine formation + reduction of imine.

c Reaction conditions: aldehyde (1.0 mmol), nitrobenzene (1.2 mmol), solvent (2 ml), and PtO2 (3 mol%) at room temperature.

a Reaction conditions: aldehyde (1.0 mmol), nitrobenzene (1.2 mmol), methanol (2 ml), and PtO2 (3 mol%) at room temperature.

b The times given correspond to the following reactions: reduction of nitroarenes + imine formation + reduction of imine.

a Reaction conditions: aldehyde (1.0 mmol), nitrobenzene (1.2 mmol), methanol (2 ml), and PtO2 (3 mol %) at room temperature.

b The times given correspond to the following reactions: reduction of nitroarenes + imine formation + reduction of imine.

c R˭tertiary butyl dimethyl silyl (TBDS).

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