Skolia Elpida, Kokotos Christoforos G
Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis 15771, Athens, Greece.
ACS Org Inorg Au. 2022 Dec 8;3(2):96-103. doi: 10.1021/acsorginorgau.2c00053. eCollection 2023 Apr 5.
Throughout the last 15 years, there has been increased research interest in the use of light promoting organic transformations. [2 + 2] Cycloadditions are usually performed photochemically; however, literature precedent on the reaction between olefins and maleimides is limited to a handful of literature examples, focusing mainly on -aliphatic maleimides or using metal catalysts for visible-light driven reactions of -aromatic maleimides. Herein, we identify the differences in reactivity between -alkyl and -aryl maleimides. For our optimized protocols, in the case of -alkyl maleimides, the reaction with alkenes proceeds under 370 nm irradiation in the absence of an external photocatalyst, leading to products in high yields. In the case of -aryl maleimides, the reaction with olefins requires thioxanthone as the photosensitizer under 440 nm irradiation.
在过去的15年里，人们对利用光促进有机转化的研究兴趣与日俱增。[2 + 2]环加成反应通常通过光化学方法进行；然而，关于烯烃与马来酰亚胺之间反应的文献先例仅限于少数几个例子，主要集中在α-脂肪族马来酰亚胺或使用金属催化剂来驱动α-芳族马来酰亚胺的可见光反应。在此，我们确定了α-烷基和α-芳基马来酰亚胺之间的反应活性差异。对于我们优化的方案，在α-烷基马来酰亚胺的情况下，与烯烃的反应在370 nm照射下且无外部光催化剂的条件下进行，可高产率地得到产物。在α-芳基马来酰亚胺的情况下，与烯烃的反应需要噻吨酮作为光敏剂，在440 nm照射下进行。
