Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH₂ or CH₃ adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl₃/Et₃N in CH₂Cl₂, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl₃ content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction.

Graphic abstract

中文翻译：

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通过 Cannizzaro、Tishchenko 和 Meerwein-Ponndorf-Verley 反应实现脂肪族和芳香族醛的歧化

通过 Cannizzaro、Tishchenko 和 Meerwein-Ponndorf-Verley 反应使醛歧化通常需要应用高温、等摩尔或过量的强碱，并且主要限于没有 CH ₂或 CH ₃与羰基相邻的醛. 在此，我们开发了一种由 AlCl ₃ /Et ₃ N in CH ₂ Cl ₂组成的高效、温和、多功能的催化体系，它可以在室温下以高产率选择性地将各种脂肪醛和芳香醛转化为相应的醇、酸和二聚酯，而不会形成通常观察到的副产物。我们还表明，较高的 AlCl ₃含量有利于向 Cannizzaro 反应的反应，而较低的含量有利于 Tishchenko 反应。此外，反应混合物中氢化物供体醇的存在将反应完全导向 Meerwein-Ponndorf-Verley 反应。

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