Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3884-3887

  Cui, Li ^a   Zhang, Guozhu ^a   Zhang, Liming ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

Catalysis; Dimerization; Gold; Homogeneity; Oxidation

Indexed keywords

ACETIC ACID DERIVATIVE; GOLD;

ARTICLE; CATALYSIS; DIMERIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

ACETATES; CATALYSIS; DIMERIZATION; GOLD; OXIDATION-REDUCTION;

EID: 67649666912     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.127     Document Type: Article

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41. For details, see the Supplementary data.
42. Although the reaction mixture is clear, filtration before the measurement using a millex syringe-driven filter unit (450 nm diameter) is necessary to get rid of the contaminating dust; otherwise, the measurement gave particle sizes of ∼700 nm, which cannot be due to gold particles as they will become visible.
43. More propargylic acetate 1 and Selectfluor were added to the filtrate, and heating the mixture led to the conversion of 1 to product 2 without further addition of any gold catalyst.
44. By forcing the instrument to perform the measurement, the result was 2.50 nm. As a control experiment, we did the same measurement of the reaction solvent (filtered), which was also used for zeroing the instrument, and an identical number (i.e., 2.50 nm) was obtained, suggesting that the machine could not effectively give negative results.