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Paper | Special issue | Vol 67, No. 2, 2006, pp.629-641
Published online, 16th September, 2005
DOI: 10.3987/COM-05-S(T)31
A Convenient Method for the Synthesis of Carboxamides and Thioesters by Using Tetrakis(2-methylimidazol-1-yl)silane

Takashi Tozawa, Yoshinobu Yamane, and Teruaki Mukaiyama*

*Center for Basic Research, The Kitasato Institute, 6-15-5 (TCI), Toshima, Kita-ku, Tokyo 114-0003, Japan


Tetrakis(2-methylimidazol-1-yl)silane [Si(2-Me-Im)4], a new dehydrating reagent having silicon–imidazole linkage, reacted readily with carboxylic acids at room temperature to form the corresponding 1-acyl-2-methylimidazole intermediates, which smoothly underwent subsequent condensation with nucleophiles such as amines or thiols to afford the corresponding carboxamides or thioesters in good to excellent yields, respectively.