Mild Conversion of Esters Lacking Acidic alpha-Hydrogens into Amides via Samarium(III) Tris[hexamethyldisilazide] and Amines

[摘要]：Samarium(III) tris[ hexamethyldisilazide] (Sm[(Me3Si)(2)N](3) = Sm[HMDS](3)) promotes the direct conversion of an ester admixed with an amine into the corresponding carboxamide under exceptionally mild conditions (<= 0 degrees C) and in high yields. Only a slight excess of amine and the lanthanide complex are required to effect complete conversion of the ester into the amide. Esters with acidic alpha-hydrogens undergo a competing Claisen-like condensation along with the desired conversion into amides.

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