Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.
Thiocarboxylates, prepared conveniently by cleavage of 9-fluorenylmethyl or trimethoxybenzyl thioesters, react at room temperature with isocyanates and isothiocyanates to give amide bonds in good to excellent yield. A carboxylate salt is also shown to react with an electron-deficient isocyanate to give the corresponding amide in excellent yield at room temperature.
Crich
David
D
Centre Scientifique de Gif, Institut de Chimie des Substances Naturelles, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr
Sasaki
Kaname
K
D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*
D000577:Amides; D000588:Amines; D017953:Isocyanates; D017879:Isothiocyanates