Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible-Light Photocatalysis
by Maity, Soumitra; Zhu, Mingzhao; Shinabery, Ryan Spencer; Zheng, Nan
N-arylcyclopropylamines c-C3H5NHR (R = Ph, 4-ClC6H4, 4-F3CC6H4, 2-PhC6H4, 1-naphthyl, 3-pyridinyl), N-arylazabicyclohexanes I (R1 = Ph, 4-BuOC6H4, 4-F3CC6H4, 4-MeOC6H4; R2 = Me, Me3C; X = CH2), and N-arylbicycloheptane I (R1 = 4-BuOC6H4; R2 = Me; R3 = H, Ph; X = CH2CH2) underwent cycloadditions with olefins such as styrene under visible light irradiation in the presence of tris(2,2'-bipyrazine)ruthenium(II) bis(hexafluorophosphate) in nitromethane to give N-arylcyclopentylamines II (R = Ph, 4-ClC6H4, 4-F3CC6H4, 2-PhC6H4, 1-naphthyl, 3-pyridinyl) and arylperhydrocyclopentapyrroles and arylperhydrocyclopentapyridines such as III (R1 = Ph, 4-BuOC6H4, 4-F3CC6H4, 4-MeOC6H4; R2 = Me, Me3C; R3 = H, Ph; X = CH2, CH2CH2) in 28-87% yields. The structure of III (R1 = Ph; R2 = Me3C; R3 = H; X = CH2) was determined by X-ray crystallog.
- Journal
- Angewandte Chemie-International Edition
- Volume
- 51
- Issue
- 1
- Year
- 2012
- Start Page
- 222-226
- URL
- https://dx.doi.org/10.1002/anie.201106162
- ISBN/ISSN
- 1521-3773; 1433-7851
- DOI
- 10.1002/anie.201106162