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Updated: Dec 10, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses
David M Whalley1, Hung A Duong, Michael F Greaney
1Institute of Chemical and Engineering Sciences (ICES) Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros, #07-01, 138665, Singapore. duong_hung@ices.a-star.edu.sg.
Abstract:
A decarboxylative, desulfonylative Smiles rearrangement is presented that employs activated-ester/energy transfer catalysis to decarboxylate β-amino acid derived starting materials at room-temperature under visible light irradiation. The radical Smiles rearrangement gives a range of biologically active arylethylamine products highly relevant to the pharmaceutical industry, chemical biology and materials science. The reaction is then applied to the synthesis of a chiral unnatural amino acid, 2-thienylalanine, used in the treatment of phenylketonuria. We also show how the reaction can proceed under metal-free and catalyst-free conditions.
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