A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses

作者：David M. Whalley, Hung A. Duong, Michael F. Greaney · 发表于：Chemical Communications · 年份：2020 · DOI：10.1039/d0cc05049k · 被引用次数：41 · 研究领域：Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques、Catalytic C–H Functionalization Methods

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.