Department of Organic Chemistry I, Joxe Mari Korta R&D Center, University of the Basque Country (UPV/EHU), Avda. Tolosa 72, 20018, Donostia-San Sebastián, Spain.
Donostia International Physics Center (DIPC), Paseo Manuel de Lardizabal 4, 20018, Donostia-San Sebastián, Spain.
Chemistry. 2021 Mar 26;27(18):5782-5789. doi: 10.1002/chem.202005338. Epub 2021 Mar 1.
The site-selective functionalization of C-H bonds within a complex molecule remains a challenging task of capital synthetic importance. Herein, an unprecedented Pd-catalyzed C(sp )-H alkoxycarbonylation of phenylalanine derivatives and other amines featuring picolinamide as the directing group (DG) is reported. This oxidative coupling is distinguished by its scalability, operational simplicity, and avoids the use of toxic carbon monoxide as the C source. Remarkably, the easy cleavage of the DG enables the efficient assembly of isoindolinone compounds. Density Functional Theory calculations support a Pd /Pd catalytic cycle.
在复杂分子中 C-H 键的选择性功能化仍然是一项具有重大合成意义的挑战性任务。在此，我们首次报道了钯催化的以吡啶甲酰胺为导向基团（DG）的苯丙氨酸衍生物和其他胺的 C(sp )-H 烷氧基羰基化反应。这种氧化偶联具有可扩展性、操作简单的特点，并且避免了使用有毒的一氧化碳作为 C 源。值得注意的是，DG 的易于裂解能够有效地构建异吲哚啉酮化合物。密度泛函理论计算支持 Pd/Pd 催化循环。
