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首页> 外文期刊>Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications >Radical alpha-alkylation of ketones with unactivated alkenes under catalytic and sustainable industrial conditions
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Radical alpha-alkylation of ketones with unactivated alkenes under catalytic and sustainable industrial conditions

机译：在催化和可持续工业条件下具有未活化的烯烃的酮的根本α-烷基化

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The industrially-viable aerobic alpha-alkylation of cyclic and acyclic ketones with allyl and alkyl alkenes in the presence of catalytic amounts of Mn2+, under homo- and heterogeneous conditions, is achieved here. The substitution of organic peroxides by Mn2+ either as a simple soluble salt or supported in zeolites, in air, generates in-situ peracid radicals and circumvents the aggressiveness of current industrial protocols, to pave the way for the design of sustainable aerobic catalytic systems. Combined reactivity and mechanistic studies show that large cyclic ketones stabilize a radical in the alpha-position due to a higher polarizability, steric hindrance and no proximity effects. As a proof of concept, the gram-scale synthesis of the industrial fragrance exaltolide is carried out with the Mn2+ catalysts in air, which clearly improves any other previously reported method not only in safety and environmental terms but also in number of synthetic steps and overall yield.
机译：在均相和非均相条件下，在催化量的Mn2+存在下，实现了环酮和无环酮与烯丙基和烷基烯烃的工业上可行的需氧α-烷基化。用Mn2+取代有机过氧化物，无论是作为一种简单的可溶性盐，还是在空气中以沸石为载体，都会产生原位过酸自由基，并绕过当前工业协议的攻击性，为设计可持续的好氧催化系统铺平道路。结合反应性和机理研究表明，大环酮由于更高的极化率、空间位阻和无邻近效应而稳定α位置的自由基。作为概念证明，工业香料麝香内酯的克级合成是在空气中使用Mn2+催化剂进行的，这明显改善了之前报道的任何其他方法，不仅在安全性和环境方面，而且在合成步骤数量和总收率方面。

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