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The Beckmann Rearrangement Executed by Visible-Light-Driven Generation of Vilsmeier-Haack Reagent

Vishnu P. Srivastava, Arvind K. Yadav, Lal Dhar S. Yadav*

*Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211002, India, Email: ldsyadavhotmail.com

V. P. Srivastava, A. K. Yadav, L. D. S. Yadav, Synlett, 2014, 25, 665-670.

DOI: 10.1055/s-0033-1340623 (free Supporting Information)


Abstract

An efficient Beckmann rearrangement at room temperature involves an eosin Y catalyzed, visible-light-mediated in situ formation of the Vilsmeier-Haack reagent from CBr4 and a catalytic amount of DMF. This operationally simple method for the activation of ketoximes avoids the need for any corrosive, water-sensitive reagents and elevated temperatures.


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Key Words

visible light, eosin Y, photoredox, Beckmann rearrangement, amides


ID: J60-Y2014