Transition-metal-catalyzed C–H bond activation/functionalization and annulation of phthalazinones,Organic & Biomolecular Chemistry

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Transition-metal-catalyzed C–H bond activation/functionalization and annulation of phthalazinones
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-09-01 , DOI: 10.1039/d1ob01616d
Chandrasekaran Sivaraj ₁ , Alagumalai Ramkumar ₁ , Nagesh Sankaran ₁ , Thirumanavelan Gandhi ₁

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Phthalazinones and their higher congeners are commonly prevalent structural motifs that occur in natural products, bioactive molecules, and pharmaceuticals. In the past few decades, transition-metal-catalyzed reactions have received an overwhelming response from organic chemists as challenging organics and heterocycles could be built with ease. Currently, the synthesis of phthalazinones largely depends on transition-metal catalysis, especially by palladium-catalyzed carbonylation. Further, the dominance of transition-metal catalysts was realized from the phthalazinones viewpoint, as nitrogen and oxygen atoms endowed upon them act as directing groups to facilitate diverse C–H activation/functionalization/annulation reactions. This highlight describes the various synthetic methods used to access phthalazinones and functionalize them by reacting with various coupling partners via chelation assistance strategy involving C(sp²)–H/N–H bond activation in the presence of transition-metal (Rh, Ru, Pd, and Ir) catalysts. The mechanisms of sulfonylation, halogenation, acylmethylation, alkylation, and annulation reactions are discussed.

中文翻译：

过渡金属催化的 C-H 键活化/功能化和酞嗪酮的环化

酞嗪酮及其高级同系物是天然产物、生物活性分子和药物中常见的普遍结构基序。在过去的几十年中，过渡金属催化反应得到了有机化学家的热烈响应，因为可以轻松构建具有挑战性的有机物和杂环化合物。目前，酞嗪酮的合成很大程度上依赖于过渡金属催化，尤其是钯催化的羰基化。此外，过渡金属催化剂的优势是从酞嗪酮的角度实现的，因为赋予它们的氮和氧原子充当引导基团以促进各种 C-H 活化/功能化/环化反应。通过在过渡金属（Rh、Ru、Pd 和 Ir）催化剂存在下的C(sp ² )-H/N-H 键活化的螯合辅助策略。讨论了磺酰化、卤化、酰基甲基化、烷基化和环化反应的机理。

更新日期：2021-09-15

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