Benzyl Palladium Intermediates: Unique and Versatile Reactive Intermediates for Aromatic Functionalization,Advanced Synthesis & Catalysis

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Benzyl Palladium Intermediates: Unique and Versatile Reactive Intermediates for Aromatic Functionalization
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-10-11 , DOI: 10.1002/adsc.202000838
Sheng Zhang ₁ , Yoshinori Yamamoto _{1,

2,

3} , Ming Bao ₁

Affiliation

Aromatic functionalizations are of current interest and importance in organic chemistry, recent transition‐metal catalyzed reactions can transform inert C−H bond into C−X (X=C, O, N, etc.) bonds, greatly enriching aromatic chemistry and related fields. Some well‐known palladium‐containing intermediates such as palladacycles and allylpalladium intermediates play an important role in organic conversions. Similar with allyl group, benzyl group also possesses the capability of stabilizing palladium through η³‐binding. In the process of the formation of benzyl palladium intermediate, there is a transition state of dearomatization. Therefore, it is a challenging and meaningful research topic to seize these aromatic destruction intermediates, realize selective functionalization reaction on aromatic ring via them, and inhibit the formation of traditional benzylated products. Herein, we summarized the recent efforts on expanding the synthetic utility, as well as exploring the mechanism in aromatic functionalization via reactive benzyl palladium intermediates. We envision that the transformation via benzyl palladium intermediates will help promote the development in the field of palladium–catalyzed aromatic regioselective functionalization.

中文翻译：

苄基钯中间体：芳香功能化的独特多功能反应中间体

芳香族官能化在有机化学中具有当前的意义和重要性，最近的过渡金属催化反应可以将惰性的C-H键转变为C-X（X = C，O，N等）键，极大地丰富了芳族化学及其相关领域。一些著名的含钯中间体，例如palladacycles和烯丙基钯中间体在有机转化中起重要作用。与烯丙基类似，苄基还可以通过具有稳定钯的能力η ³-捆绑。在形成苄基钯中间体的过程中，存在脱芳香化的过渡态。因此，抓住这些芳族破坏中间体，通过它们实现对芳环的选择性官能化反应，抑制传统苄基化产物的形成，是一个具有挑战性和有意义的研究课题。在这里，我们总结了最近在扩大合成用途方面的努力，以及通过反应性苄基钯中间体探索芳族官能化的机理。我们设想通过苄基钯中间体进行的转化将有助于促进钯催化的芳族区域选择性功能化领域的发展。

更新日期：2020-10-11

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