Stoichiometric Reductive CN Bond Formation of Arylgold(III) Complexes with N-Nucleophiles

✍ Scribed by Séverine Lavy; Jeremie J. Miller; Marek Pažický; Anne-Sophie Rodrigues; Frank Rominger; Christoph Jäkel; Daniel Serra; Nikolai Vinokurov; Michael Limbach

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 410 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201000598

✦ Synopsis

Abstract

The reductive formation of substituted anilines from amines and three well‐defined aryl‐ gold(III) complexes, i.e., dichloro(2,6‐lutidine)phen‐ ylgold(III) (2), dichloro(2,6‐lutidine)‐p‐tolylgold(III) (3), and chlorobis(triphenylphosphine)phenylgold(III) chloride (4) was studied. The reaction is stoichiometric in gold and represents a key step of a potential gold‐catalyzed intermolecular amination reaction of arenes. It proceeds smoothly with a broad range of N‐nucleophiles in the presence of sodium acetate (NaOAc) and enables the selective formation of N‐substituted anilines in good yields. A mechanistic pathway is proposed and discussed as well.