Au(I)-catalyzed highly efficient intermolecular hydroamination of alkynes

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3349-3352

  Mizushima, Eiichiro ^a   Hayashi, Teruyuki ^a   Tanaka, Masato ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANILINE DERIVATIVE; GOLD; IMINE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; HYDROAMINATION;

EID: 0141744599     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0353159     Document Type: Article

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46. 40 (30 mg, 0.01 mmol) was stirred at 70°C for 14 h. After the mixture was cooled, hexane (25 mL) was added to the reaction mixture to precipitate out a white powder. The powder was recrystallized from hexane-dichloromethane to give 4-bromo-N-(α-methylbenzylidene)aniline (4. 9 g, 18 mmol, 85% isolated yield).
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49. 12]-catalyzed hydroamination; see ref 12b.
50. In the gold(III)-catalyzed intramolecular hydroamination to afford cyclic imines, direct attack of amine to the coordinated alkyne was illustrated; see ref 16. On the other hand, in the gold(I)-catalyzed methanol addition to alkynes, an associative mechanism involving coordination of methanol to gold was predicted by ab initio calculations; see ref 16b.