Catalytic Transamidation Reactions Compatible with Tertiary Amide Metathesis under Ambient Conditions
Catalytic Transamidation Reactions Compatible with Tertiary Amide Metathesis under Ambient Conditions
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DOI：
10.1021/ja8094262
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发表时间：
2009-07-29
影响因子：
15
通讯作者：
Stahl, Shannon S.
中科院分区：
文献类型：
--
作者：
Stephenson, Nickeisha A.;Zhu, Jiang;Stahl, Shannon S.
羧酰胺的碳-氮键在大多数条件下非常稳定。本研究表明，简单的锆和铌的酰胺配合物是高效的催化剂的平衡控制的仲胺和叔酰胺之间的转酰胺反应。在许多情况下，转酰胺作用在室温下快速进行。我们发现，这些新的催化剂是足够的活性，以促进复分解的叔酰胺，这是从连续的转酰胺基循环。我们观察到的催化活性是前所未有的，并代表了一个重大的一步，进行平衡控制的反应与羧酰胺的长期目标。
The carbon-nitrogen bond of carboxamides is extremely stable under most conditions. The present study reveals that simple zirconium- and hafnium-amido complexes are highly efficient catalysts for equilibrium-controlled transamidation reactions between secondary amines and tertiary amides. In a number of cases, transamidation proceeds rapidly at room temperature. We find that these new catalysts are sufficiently active to promote the metathesis of tertiary amides, which arises from successive transamidation cycles. The catalytic activities we observe are unprecedented and represent a substantial step toward a long-range goal of conducting equilibrium-controlled reactions with carboxamides.