Synlett 2007(16): 2557-2558  
DOI: 10.1055/s-2007-986628
LETTER
© Georg Thieme Verlag Stuttgart · New York

Molybdenum Hexacarbonyl and DBU Reduction of Nitro Compounds under Microwave Irradiation

John Spencer*, Nazira Anjum, Hiren Patel, Rajendra P. Rathnam, Jason Verma
School of Science, University of Greenwich at Medway, Chatham Maritime, Kent, ME4 4TB, UK
Fax: +44(208)3319805; e-Mail: j.spencer@gre.ac.uk;
Further Information

Publication History

Received 5 July 2007
Publication Date:
23 August 2007 (online)

Abstract

An ethanolic mixture of molybdenum hexacarbonyl and DBU mediates the reduction of nitroarenes to the corresponding anilines in excellent yields in 15-30 minutes under microwave ­irradiation.

    References and Notes

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    Typical Work-up
    After solvent concentration, the resulting crude product is passed over a short SiO2 plug (6 cm × 3 cm). Typical eluent: neat CH2Cl2 to 5:1 CH2Cl2-acetone gradient. All products were characterised by 1H NMR, 13C NMR, GC-MS, or MS and correspond to commercial samples or literature values (see ref. 7b and also ref. 9). Compound 2o: 1H NMR (270 MHz): δ = 3.67 (2 H, br s), 4.67 (2 H, s), 6.54 (1 H, d, J = 8.4 Hz), 6.78 (1 H,s), 7.07 (1 H, s), 7.11 (1 H, s). 13C NMR (67 MHz): δ = 62.9, 115.1, 121.1, 129.8, 138.7, 145.4.

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  • Similar ‘multifunctional’ nitro analogues were selectively reduced with H2 in the presence of catalytic gold nanoparticles:
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  • 9b See also: Blaser HU. Science  2006,  313:  312 ; and references cited therein
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8

Spencer, J.; Rathnam, R. P.; Patel, H.; Anjum, N., manuscript in preparation.