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Issue 8, 2015
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Highly chemo- and regioselective allylic substitution with tautomerizable heteroarenes

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Abstract

Tautomerizable heteroarenes, bearing multiple interconvertible nucleophilic centers exhibit high chemo- and regioselective allylation irrespective of allylating agents used under Pd-catalysis. The achieved selectivity may be attributed to the dominant lactam form of heteroarenes and Pd-catalyzed intramolecular allylic substitution. A generalized green protocol for chemo- and regioselective allylation of biologically relevant heteroarenes with allyl alcohols in dimethyl carbonate (DMC) as solvent was developed. Excellent selectivity was observed during intermolecular competition study demonstrating the differential nucleophilicity of tautomerizable heteroarenes and differential allyl palladium forming ability of a variety of allyl alcohols.

Graphical abstract: Highly chemo- and regioselective allylic substitution with tautomerizable heteroarenes

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Article information


Submitted
14 May 2015
Accepted
17 Jun 2015
First published
17 Jun 2015

Green Chem., 2015,17, 4300-4306
Article type
Paper
Author version available

Highly chemo- and regioselective allylic substitution with tautomerizable heteroarenes

D. Kumar, S. R. Vemula and G. R. Cook, Green Chem., 2015, 17, 4300
DOI: 10.1039/C5GC01028D

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