Palladium-catalyzed carbonylation of activated alkyl halides via radical intermediates,Industrial Chemistry & Materials

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Palladium-catalyzed carbonylation of activated alkyl halides via radical intermediates
Industrial Chemistry & Materials Pub Date : 2023-08-16 , DOI: 10.1039/d3im00078h
Zhi-Peng Bao _{1,

2} , Xiao-Feng Wu _{1,

2}

Affiliation

Palladium-catalyzed carbonylation is an efficient approach to prepare carbonyl-containing compounds with high atomic economy in synthetic organic chemistry. However, in comparison with aryl halides, carbonylation of alkyl halides is relatively challenging due to the decreased stability of the palladium intermediates. Carbonylation of activated alkyl halides is even more difficult, as nucleophilic substitution reactions with nucleophiles occur more easily with them. In this article, we summarize and discuss recent achievements in palladium-catalyzed carbonylative reactions of activated alkyl halides. The transformations proceed through radical intermediates which are generated in various manners. Under a relatively high pressure of carbon monoxide, the corresponding aliphatic carboxylic acid derivates were effectively prepared with various nucleophiles as the reaction partners. Besides alcohols, amines and organoboron reagents, four-component reactions in combination with alkenes or alkynes were also developed. Case-by-case reaction mechanisms are discussed as well and a personal outlook has also been provided.

中文翻译：

钯催化通过自由基中间体活化卤代烷的羰基化

钯催化的羰基化是合成有机化学中制备具有高原子经济性的含羰基化合物的有效方法。然而，与芳基卤化物相比，由于钯中间体的稳定性降低，烷基卤化物的羰基化相对具有挑战性。活化的烷基卤化物的羰基化甚至更加困难，因为它们更容易与亲核试剂发生亲核取代反应。在本文中，我们总结并讨论了钯催化活化卤代烷羰基化反应的最新成果。转化通过以各种方式产生的自由基中间体进行。在较高的一氧化碳压力下，以各种亲核试剂为反应对象，有效地制备了相应的脂肪族羧酸衍生物。除了醇、胺和有机硼试剂外，还开发了与烯烃或炔烃组合的四组分反应。还讨论了具体情况的反应机制，并提供了个人观点。

更新日期：2023-08-16

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