α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid

✍ Scribed by Patrick Y.S Lam; Sophie Deudon; Elisabeth Hauptman; Charles G Clark

• Book ID: 104230277
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 75 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00203-9

✦ Synopsis

Heteroarylcarboxamides containing a-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The a-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other a-nitrogen functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation.