Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling

A copper‐catalyzed coupling of aryl, heteroaryl, and vinyl iodides with α‐silyldifluoroamides is reported. The reaction forms α,α‐difluoro‐α‐aryl amides from electron‐rich, electron‐poor, and sterically hindered aryl iodides in high yield and tolerates a variety of functional groups. The aryldifluor...

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Bibliographic Details
Published in:Angewandte Chemie 2016-03, Vol.128 (14), p.4643-4648
Main Authors: Arlow, Sophie I., Hartwig, John F.
Format: Article
Language:eng ; ger
Subjects:
Amide
Amides
Aromatic compounds
Arrays
Chemistry
Coupling
Cross coupling
Fluor
Functional groups
Iodides
Kreuzkupplungen
Kupfer
Synthesemethoden
Synthesis
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Summary:A copper‐catalyzed coupling of aryl, heteroaryl, and vinyl iodides with α‐silyldifluoroamides is reported. The reaction forms α,α‐difluoro‐α‐aryl amides from electron‐rich, electron‐poor, and sterically hindered aryl iodides in high yield and tolerates a variety of functional groups. The aryldifluoroamide products can be transformed further to provide access to a diverse array of difluoroalkylarenes, including compounds of potential biological interest. (Hetero)Aryl‐ und Vinyliodide wurden unter Kupferkatalyse mit α‐Silyldifluoramiden gekuppelt. Elektronenreiche, elektronenarme und sterisch gehinderte Aryliodide mit verschiedenen funktionellen Gruppen ergeben α,α‐Difluor‐α‐arylamide in hohen Ausbeuten. Ausgehend von den Produkten sind diverse Difluoralkylarene zugänglich. TMS=Trimethylsilyl.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201600105