Photochemical C(sp3)–H Activation for Diversity-Oriented Synthesis of 3-Functionalized Oxindoles,The Journal of Organic Chemistry

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Photochemical C(sp3)–H Activation for Diversity-Oriented Synthesis of 3-Functionalized Oxindoles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-03-05 , DOI: 10.1021/acs.joc.3c02953
Hao Hou ₁ , Wei Ou ₁ , Chenliang Su ₁

Affiliation

Heteroatom-adjacent C(sp³) radical cyclization of N-arylacrylamides provides a straightforward pathway to synthesize valuable 3-functionalized oxindoles. Traditional cyclization reactions normally require harsh conditions or transition-metal catalysts. Here, we developed a metal-free, diversity-oriented synthesis of 3-functionalized oxindoles via photochemically induced selective cleavage of C(sp³)–H bonds. A variety of 3-substituted oxindoles with functionalities such as ethers, polyhalogens, benzyl, and formyl groups can be obtained by a rational design. This strategy is characterized by its simple operation and mild conditions, aligning well with the developmental requirements for sustainable chemistry. The gram-scale continuous-flow synthesis and efficient construction of bioactive molecules highlight its practical utility.

中文翻译：

光化学 C(sp3)–H 活化用于 3-官能化羟吲哚的多样性合成

N-芳基丙烯酰胺的杂原子相邻C(sp ³ )自由基环化提供了合成有价值的3-官能化羟吲哚的直接途径。传统的环化反应通常需要苛刻的条件或过渡金属催化剂。在这里，我们通过光化学诱导 C(sp ³ )–H 键的选择性裂解，开发了一种无金属、多样性导向的 3 功能化羟吲哚合成方法。通过合理设计可以得到多种具有醚、多卤、苄基、甲酰基等官能团的3-取代羟吲哚。该策略操作简单、条件温和，符合可持续化学的发展要求。克级连续流动合成和生物活性分子的高效构建凸显了其实用性。

更新日期：2024-03-05

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