Expeditious synthesis of N0-substituted N-mesitylimidazolium salts as NHC precursors

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 5041-5043

  Truscott, Byron J ^a   Klein, Rosalyn ^a   Kaye, Perry T ^a  

^a RHODES UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; IMIDAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; COMPLEX FORMATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 78549234004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.097     Document Type: Article

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36. 2O to give the desired N0-substituted N-mesitylimidazolium salts 8-15. Alkylations were typically repeated using 100-250 mg of the starting material. The largest quantity of starting material used in a reaction was 500 mg and the reaction proceeded as normal.
37. 2), 122.4 and 123.0 (2 × d, C-4 and C-5), 129.8 (d, 2 × ArCH), 130.8 (s, ArC), 134.2 (s, 2 × ArC), 139.2 (d, NCHN), 141.3 (s, ArC) and 168.9 (s, 2 × C=O).
38. 2-Et2O).
39. 2-Et2O) (lit.,15 237-238 °C). 1-[(1-Ethoxycarbonyl)ethyl]-3-mesitylimidazol-2-ium bromide 1218 (69 mg, 77%), yellow oil.
40. 2), 122.4 (d, NCH), 123.0 (d, NCH), 129.9 (d, 2 × ArCH), 130.7 (s, ArC), 134.2 (s, 2 × ArC), 138.6 (d, NCHN) and 141.4 (s, ArC).
41. 2), 122.9 (d, 2 × C-40), 124.8 (d, 2 × C-50), 129.7 (d, 4 × ArCH), 130.6 (s, 2 × ArC), 134.1 (s, 4 × ArC), 137.1 (d, 2 × C-20) and 141.2 (s, 2 × ArC).
42. Song, L.; Luo, X.; Wang, Y.; Gai, B.; Hu, Q. J. Organomet. Chem. 2009, 694, 103-112. Compound 15 was reported as the dibromide salt.