Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy.
Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy.
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本文报道了在正庚烷中，以水分子为促进剂，用π-苄基钯体系进行脱水N-苄基化反应的合成方法。水的存在显著加速了碳-氮键的形成，这在原子经济的过程中完成，以提供相应的N-单苄基化产物。交叉实验提供了H/D乱序产物，这与借氢机制一致。动力学同位素效应的测量结果表明，苄型碳-氢键断裂是速率决定步骤。我们描述了一种新的策略，在庚烷中的水促进脱水偶联反应，这提供了一个可持续的直接胺化醇。
A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon–nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon–hydrogen bond cleavage was the rate-determining step. We describe a novel strategy for the water-promoted dehydrative coupling reaction in heptane, which offers a sustainable direct amination of alcohols.
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