Visible-light organophotoredox-mediated intermolecular formal [4 + 2] cycloadditions of arylcyclobutylamines with olefins

• Published in: Organic & biomolecular chemistry Vol. 21; no. 22; pp. 4637 - 4642
• Main Authors: Luo, Zhengshan, Xing, Zequn, Gao, Rui, Han, Yufang, Ren, Jun, Wang, Zhongwen
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 07.06.2023; Royal Society of Chemistry
• Subjects: Alkenes; Chemistry; Chemistry, Organic; Cycloaddition; Physical Sciences; Potassium phosphate; Potassium phosphates; Science & Technology; Sulfonylurea; DESIGN; ACID; CYCLOBUTYLANILINES; ANNULATION; C-C BOND; PHOTOREDOX CATALYSIS
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00527e

We have developed a visible-light-mediated formal [4 + 2] cycloaddition of arylcyclobutylamines with olefins, using QXPT-NPhCN as an organic photocatalyst. The corresponding cycloadducts could be obtained from electron-deficient olefins, aryl olefins and exocyclic olefins. We found that the addition of K 3 PO 4 could significantly promote the cycloadditions. Using this method, 2-functionalized cyclohexylamines including the ones with spiro-skeletons can be expediently obtained. Based on the "3D-bioisostere" principle, we designed and synthesized three cyclohexylamine 2-sulfonylurea compounds. With QXPT-NPhCN as an organic photocatalyst, we have developed visible-light-mediated formal [4 + 2] cycloaddition of arylcyclobutylamines with olefins to effectively afford 2-functionalized cyclohexylamines.