Polytriazoles as copper(I)-stabilizing ligands in catalysis

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2853-2855

  Chan, Timothy R ^a   Hilgraf, Robert ^a   Sharpless, K Barry ^a   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; AZIDE; COPPER; LIGAND; POLYTRIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; LIGATION; OXIDATION; SYNTHESIS;

AMINES; CATALYSIS; COPPER; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYMERS; TRIAZOLES;

EID: 4444324951     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0493094     Document Type: Article

References (24)

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22. While bis-triazoles from entries 2 and 3 show a stronger ligand-accelerating effect, they are not as potent in protecting the copper(I) oxidation state. This was also confirmed by further reducing the amount of the copper catalyst to 0.25 mol %. TBTA clearly outperformed all other ligands.
23. 10: C, 67.90; H, 5.70; N, 26.40. Found: C, 67.71; H, 5.73; N, 26.32. Analytically pure sample could be obtained by recrystallization of 1.00 g of TBTA from a hot 1:1 tert-butyl alcohol/water solution (40 mL), followed by filtration and washing with water (2 x 20 mL). The white needlelike crystals were dried under high vacuum overnight. Yield: 0.86 g, 86%.
24. Similar mode of binding has been previously suggested for trisoxazoline-based ligands. See: Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941.