School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Org Lett. 2011 Oct 7;13(19):5326-9. doi: 10.1021/ol202187h. Epub 2011 Sep 12.
A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O(2), leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.
本文提出了一种新的钯（II）催化 N-烷氧基苯甲酰胺直接合成亚烷基异吲哚啉酮的方法。异吲哚啉酮的形成通过高效和 E-选择性的 C-H 活化/Heck/Aza-Wacker 序列进行。在与 O(2) 协同的氧化体系中，可以使用亚化学计量的苯醌，从而易于纯化产物。通过与 CO 进行羰基化反应，改变反应条件为取代的邻苯二甲酰亚胺提供了一种通用途径。这两个体系都被发现能够容忍广泛的官能团。
