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Metal-Free Transfer Hydrogenation of Nitroarenes in Water with Vasicine: Revelation of Organocatalytic Facet of an Abundant Alkaloid

Sushila Sharma, Manoranjan Kumar, Vishal Kumar and Neeraj Kumar*

*Natural Plant Products Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India, Email: neerajihbt.res.in

S. Sharma, M. Kumar, V. Kumar, N. Kumar, J. Org. Chem., 2014, 79, 9433-9439.

DOI: 10.1021/jo5019415 (free Supporting Information)


Abstract

Vasicine, an abundantly available quinazoline alkaloid from the leaves of Adhatoda vasica, enables an efficient metal- and base-free reduction of nitroarenes to the corresponding anilines in water. The chemoselective method tolerates a wide range of reducible functional groups, such as ketones, nitriles, esters, halogens, and heterocyclic rings. Dinitroarenes are reduced selectively to the corresponding nitroanilines.

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degradation of vasicine



Key Words

reduction of nitro compounds, green chemistry, vasicine


ID: J42-Y2014