Stoichiometric Reductive CN Bond Formation of Arylgold(III) Complexes with <i>N</i>‐Nucleophiles

Séverine Lavy, Jeremie J. Miller, M. Pazicky, A.-S. Rodrigues, Frank Röminger, C. Jakel, D. Serra, Michael Limbach

Advanced Synthesis & Catalysis · 2010 · 51 citations · 50 references

Concepts

Abstract

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.

References

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