Nucleophilic Attack in Methoxycarbenes: Heterolytic Cleavage of the Carbon (sp 3 )–Oxygen Bond versus Aminolysis
2013; American Chemical Society; Volume: 32; Issue: 15 Linguagem: Inglês
10.1021/om400565c
ISSN1520-6041
AutoresMaría Talavera, S. Bolaño, Jorge Bravo, Jesús Castro, Soledad García‐Fontán, José M. Hermida‐Ramón,
Tópico(s)Catalytic Cross-Coupling Reactions
ResumoThe iridium methoxycarbene [IrCp*Cl{═C(OMe)CH═CPh2}(PPh2Me)]PF6 (3) can undergo a clean attack by nucleophiles at least by two different pathways: (1) an unusual nucleophilic attack of primary, secondary, and tertiary amines at the sp3 carbon–oxygen bond, which gives an acyl complex and amine alkylation and (2) a nucleophilic attack of the ammonia at the carbenic carbon, which forms a primary aminocarbene.
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