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Intermolecular Difunctionalization of C,C-Palladacycles Obtained by Pd(0)-Catalyzed C–H Activation
Accounts of Chemical Research ( IF 18.3 ) Pub Date : 2022-11-15 , DOI: 10.1021/acs.accounts.2c00627
Yanghui Zhang 1
Affiliation  

C,C-Palladacycles are an important class of organometallic compounds in which palladium is σ-bonded to two carbon atoms. They have three notable features that make them attractive in organic synthesis and organometallic chemistry: (1) C,C-Palladacycles are reactive intermediates that can be accessed via Pd(0)-catalyzed C–H activation of organic halides. Compared to Pd(II)-catalyzed heteroatom-directed C–H activation, C–H activation catalyzed by Pd(0) has some distinct advantages. In this type of catalytic reaction, the halo groups of readily available organic halides act as traceless directing groups. Furthermore, this strategy avoids the use of stoichiometric external oxidants. (2) C,C-Palladacycles have differentiated reactivities from common open-chain Pd(II) species. In particular, C,C-palladacycles have high reactivity toward electrophiles including alkyl halides. This unique reactivity can be utilized to develop novel reactions. (3) C,C-Palladacycles have two C–Pd bonds, providing a unique platform for developing novel reactions.

中文翻译:

Pd(0)-催化的 C-H 活化获得的 C,C-钯环的分子间双功能化

C , C -Palladacycles 是一类重要的有机金属化合物,其中钯与两个碳原子成 σ 键。它们具有三个显着特征,使它们在有机合成和有机金属化学中具有吸引力:(1) C , C -Palladacycles 是反应性中间体,可以通过 Pd(0) 催化的有机卤化物的 C-H 活化获得。与 Pd(II) 催化的杂原子定向 C-H 活化相比,Pd(0) 催化的 C-H 活化具有一些明显的优势。在这种类型的催化反应中,容易获得的有机卤化物的卤素基团充当无痕导向基团。此外,该策略避免使用化学计量的外部氧化剂。(2) C , C-Palladacycles 与常见的开链 Pd(II) 物种具有不同的反应性。特别是,CC-钯环对亲电子试剂(包括卤代烷)具有高反应性。这种独特的反应性可用于开发新的反应。(3) C , C -Palladacycles 有两个 C-Pd 键,为开发新反应提供了独特的平台。
更新日期:2022-11-15
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