Synthesis of Highly Functionalized N,N‐Diarylamides by an Anodic C,N‐Coupling Reaction

• Published in: Chemistry : a European journal Vol. 25; no. 33; pp. 7835 - 7838
• Main Authors: Dörr, Maurice, Lips, Sebastian, Martínez‐Huitle, Carlos Alberto, Schollmeyer, Dieter, Franke, Robert, Waldvogel, Siegfried R.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 12.06.2019; Wiley Subscription Services, Inc
• Subjects: C,N-coupling; Chemistry; Chemistry, Multidisciplinary; C−H activation; electrochemistry; Hydroxyl groups; oxidation; Physical Sciences; Science & Technology; Substrates; sustainable chemistry; AMINATION; C-H activation; C,N-coupling; electrochemistry; ONE-POT SYNTHESIS; PHENOLS; oxidation; BENZOXAZOLES; sustainable chemistry; C−H activation
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201901442

We report an innovative, sustainable and straightforward protocol for the synthesis of N,N‐diarylamides equipped with nonprotected hydroxyl groups by using electrosynthesis. The concept allows the application of various substrates furnishing diarylamides with yields up to 57 % within a single and direct electrolytic protocol. The method is thereby easy to conduct in an undivided cell with constant current conditions offering a versatile and short‐cut alternative to conventional pathways. C−H activation: Electrochemical, dehydrogenative C,N‐coupling can be conducted in a simple undivided cell and is scalable and inherently safe providing highly substituted diarylamides (see scheme).