Catalytic ester-amide exchange using group (IV) metal alkoxide-activator complexes |
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Authors: | Han Chong Lee Jonathan P Lobkovsky Emil Porco John A |
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Affiliation: | Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA. |
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Abstract: | A process for preparation of amides from unactivated esters and amines has been developed using a catalytic system comprised of group (IV) metal alkoxides in conjunction with additives including 1-hydroxy-7-azabenzotriazole (HOAt). In general, ester-amide exchange proceeds using a variety of structurally diverse esters and amines without azeotropic reflux to remove the alcohol byproduct. Initial mechanistic studies on the Zr(Ot-Bu)4-HOAt system revealed that the active catalyst is a novel, dimeric zirconium complex as determined by X-ray crystallography. |
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