Department of Chemistry, University of Delhi, Delhi 110007, India.
Institut für Organische Chemie, Universität Regensburg, Universitätsstr, 93053 Regensburg, Germany.
J Org Chem. 2022 May 6;87(9):6263-6272. doi: 10.1021/acs.joc.2c00491. Epub 2022 Apr 27.
Copper-catalyzed [3 + 2] cycloadditions of -tosylcyclopropylamine with alkynes and alkenes have been accomplished under visible light irradiation. The developed approach is compatible with a range of functionalities and allows the synthesis of diversified aminated cyclopentene and cyclopentane derivatives being relevant for drug synthesis. The protocol is operationally simple and economically affordable as it does not require any ligand, base, or additives. As the key step, the one-electron oxidation of the -tosyl moiety by visible light-induced homolysis of a transient Cu(II)-tosylamide complex is proposed, providing a facile entry for -centered radicals.
在可见光照射下，实现了 -甲苯磺酰基环丙胺与炔烃和烯烃的铜催化 [3 + 2]环加成反应。所开发的方法与多种官能团兼容，并允许合成多样化的氨基环戊烯和环戊烷衍生物，这些衍生物与药物合成有关。该方案操作简单，经济实惠，因为它不需要任何配体、碱或添加剂。作为关键步骤，通过瞬态 Cu(II)-甲苯磺酰胺配合物的可见光诱导均裂，实现了对 -甲苯磺酰基部分的单电子氧化，为 -中心自由基提供了一个简单的入口。
