Doan Son H, Hussein Mohanad A, Nguyen Thanh Vinh
School of Chemistry, University of New South Wales, Sydney, Australia.
Chem Commun (Camb). 2021 Sep 6;57(71):8901-8904. doi: 10.1039/d1cc02947a.
The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuable -alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.
Ritter反应曾经是使醇和腈官能化的最强大的合成工具之一，可提供有价值的α-烷基酰胺产物。然而，由于该反应使用强酸性和苛刻的反应条件，常常导致复杂的副反应，因此在现代有机合成中并不常用。在此，我们报道了一种使用环庚三烯正离子盐促进Ritter反应的新方法。该方法对一系列醇和腈底物都有效，能以良好至优异的产率得到相应产物。此反应方案适用于微波和连续流动反应器，为在有机合成中的进一步应用提供了一个有吸引力的机会。
