Copper‐Catalyzed Trifluoromethylation of Aliphatic N‐Arylhydrazones: A Concise Synthetic Entry to 2‐Trifluoromethylindoles from Simple Aldehydes. Issue 13 (11th September 2015)

• Record Type: Journal Article
• Authors: Prieto, Alexis; Landart, Mélissa; Baudoin, Olivier; Monteiro, Nuno; Bouyssi, Didier
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 13(2015)
• Page Start: 2939
• Page End: 2943
• Publication Date: 2015-09-11
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500237
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The copper‐catalyzed C(<italic>sp</italic>²)H trifluoromethylation of <italic>N, N</italic>‐disubstituted hydrazones using the Togni reagent is demonstrated to proceed efficiently for aliphatic aldehyde‐derived substrates. The success of the reactions relied on the choice of the <italic>N, N</italic>‐diphenylamino group as the terminal hydrazone amino group where <italic>N, N</italic>‐dialkylamino groups were preferred for (hetero)aromatic aldehyde‐derived substrates. In addition, the trifluoromethylated <italic>N</italic>‐arylhydrazones are shown to be ideal substrates for Fischer indole synthesis allowing a straightforward, three‐step access to 2‐trifluoromethylindole derivatives from simple aldehydes.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj2n0t61vg" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>