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Stoichiometric Reductive CN Bond Formation of Arylgold(III) Complexes with N ‐Nucleophiles
Author(s) -
Lavy Séverine,
Miller Jeremie J.,
Pažický Marek,
Rodrigues AnneSophie,
Rominger Frank,
Jäkel Christoph,
Serra Daniel,
Vinokurov Nikolai,
Limbach Michael
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000598
Subject(s) - chemistry , nucleophile , stoichiometry , triphenylphosphine , aryl , amination , medicinal chemistry , reductive amination , intermolecular force , reductive elimination , polymer chemistry , catalysis , organic chemistry , molecule , alkyl
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.