Visible-Light-Driven [3 + 2]/[4 + 2] Annulation Reactions of Alkenes with N-Aminopyridinium Salts,Organic Letters

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Visible-Light-Driven [3 + 2]/[4 + 2] Annulation Reactions of Alkenes with N-Aminopyridinium Salts
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-05 , DOI: 10.1021/acs.orglett.2c02323
Yu-Zhao Wang ₁ , Peng-Yu Liang ₁ , Hong-Chao Liu ₁ , Wu-Jie Lin ₁ , Pan-Pan Zhou ₁ , Wei Yu ₁

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The annulation reactions of benzoamidyl radicals with alkenes were realized under visible light irradiation with fac-Ir(ppy)₃ as catalyst and N-aminopyridinium salts as benzoamidyl radical precursors. The reaction can deliver two distinct types of products: in the case of vinyl arenes, [3 + 2] annulation product dihydrooxazoles were yielded exclusively; when alkyl-substituted alkenes were used, on the other hand, it afforded [4 + 2] annulation product dihydroisoquinolinones. Factors determining the reaction consequence were elucidated by DFT calculations.

中文翻译：

烯烃与 N-氨基吡啶鎓盐的可见光驱动 [3 + 2]/[4 + 2] 环化反应

以fac -Ir(ppy) ₃为催化剂，N-氨基吡啶鎓盐为苯甲酰胺自由基前体，在可见光照射下实现了苯甲酰胺自由基与烯烃的环化反应。该反应可以产生两种不同类型的产物：在乙烯基芳烃的情况下，仅产生 [3 + 2] 环化产物二氢恶唑；另一方面，当使用烷基取代的烯烃时，它提供了[4 + 2]环化产物二氢异喹啉酮。通过 DFT 计算阐明了决定反应后果的因素。

更新日期：2022-08-05

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