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TMS-Diazomethane-Mediated Thione Dimerization Enables Access to Photoconvertible Diazaxanthilidene Dyes for Live-Cell

Joao Luiz P de Albuquerque1, Christopher L Johnny1, Leah G Raizen1

  • 1Chemistry Department, University of Pennsylvania, 231 S 34th Street, Philadelphia19104, Pennsylvania, United States.

Organic Letters
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PubMed

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...