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Updated: Jun 21, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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桑德迈尔硫化 (异质) 芳氨基使用DABSO作为SO2替代物

Lucia Pincekova1, Aurélien Merot2, Gabriel Schäfer2

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K.

Organic letters
|July 11, 2024
PubMed
概括

一种新的桑德梅耶尔类反应使得使用DABSO作为二氧化硫替代品,从anilin中合成硫尼尔化物. 这种可扩展的方法为药物发现提供了直接访问有价值的硫胺.

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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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...
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