Blue Light-Promoted Reaction of α-Diazoketones and Sulfoxonium Ylides: Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides,Advanced Synthesis & Catalysis

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Blue Light-Promoted Reaction of α-Diazoketones and Sulfoxonium Ylides: Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-10-20 , DOI: 10.1002/adsc.202200944
Yirong Dong ₁ , Yu Tian ₁ , Zunting Zhang ₁ , Tao Wang ₁

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We report a strategy for the preparation of 1,3-dicarbonyl sulfoxonium ylides from α-diazoketones and sulfoxonium ylides. The transformation is achieved based on the blue-LEDs-promoted Wolff rearrangement of the α-diazoketones, and the nucleophilic nature of the sulfoxonium ylides. A large array of products was prepared to demonstrate the substrate scope and functional group tolerance. A plausible mechanism was proposed for this transformation based on the experimental results. Furthermore, the synthetic utility of the products was explored.

中文翻译：

蓝光促进 α-重氮酮与叶立德的反应：1,3-二羰基叶立德的合成

我们报告了从 α-重氮酮和氧化亚砜叶立德制备 1,3-二羰基氧化亚砜叶立德的策略。这种转变是基于蓝色 LED 促进的 α-重氮酮的 Wolff 重排和氧化亚硝叶立德的亲核性质实现的。准备了大量的产品来展示底物范围和官能团耐受性。根据实验结果，为这种转变提出了一种似是而非的机制。此外，探索了产品的合成效用。

更新日期：2022-10-20

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