An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction |
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Authors: | Arun K. Sinha Vinod Kumar Abhishek Sharma Anuj Sharma Rakesh Kumar |
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Affiliation: | Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur 176061, Himachal Pradesh, India |
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Abstract: | A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation-decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic acid reveals an interesting facet to the classical Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in the form of quinoline/Cu salt, and the requirement for harsh protection-deprotection steps for the synthesis of hydroxylated stilbenes. |
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Keywords: | (E)-Stilbenes Perkin reaction Decarboxylation C-C coupling Microwave |
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