Gold-catalyzed intermolecular hydroamination of allenes: First example of the use of an aliphatic amine in hydroamination

Synlett

Volumn , Issue 11, 2007, Pages 1767-1770

  Nishina, Naoko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Aliphatic amine; Allenes; Gold catalyst; Gold phosphine complex; Hydroamination

Indexed keywords

ALIPHATIC AMINE; ALLENE DERIVATIVE; GOLD COMPLEX; MORPHOLINE; PHOSPHINE; TOLUENE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 34447545554     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984501     Document Type: Article

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58. 4.
59. 2(o-tolyl)] (25.4 mg, 0.05 mmol) in toluene (0.5 mL) was added morpholine (43.7 mg, 0.502 mmol). To the reaction mixture was added 4-methylphenylallene (1a, 79.3 mg, 0.6 mmol) and the resulting mixture was stirred at 80°C under an Ar atmosphere. The reaction mixture was colorless and heterogeneous at the beginning, but it turned yellow to brown as the reaction progressed. After the reaction was completed (12 h), the reaction mixture was filtered through short Florisil® gel pad with EtOAc as an eluent and the resulting filtered solution was concentrated. The product was purified by column chromatography (basic silica gel, hexane-EtOAc = 100:1 to 10:1) to give 3a in 83% yield (90.8 mg).
60. 3): δ = 2.05 (E- and Z-3 H, s), 2.25-2.42 (Z-4 H, m), 2.44-2.60 (E-4 H, m), 2.91 (Z-2 H, d, J = 6.8 Hz)