Stoichiometric Reductive CN Bond Formation of Arylgold(III) Complexes with  N ‐Nucleophiles | Zendy

Lavy Séverine | Zendy; Miller Jeremie J. | Zendy; Pažický Marek | Zendy; Rodrigues AnneSophie | Zendy; Rominger Frank | Zendy; Jäkel Christoph | Zendy; Serra Daniel | Zendy; Vinokurov Nikolai | Zendy; Limbach Michael | Zendy

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Stoichiometric Reductive CN 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.

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