Visible-Light Organophotoredox-Mediated [3 + 2] Cycloaddition of Arylcyclopropylamine with Structurally Diverse Olefins for the Construction of Cyclopentylamines and Spiro[4.<i>n</i>] Skeletons
Zhengshan Luo, Bowen Cao, Tianhang Song, Zequn Xing, Jun Ren, Zhongwen Wang
Abstract
We developed a visible-light-mediated [3 + 2] cycloaddition of arylcyclopropylamine with structurally diverse olefins using QXPT-NPh as a highly efficient organic photoredox catalyst. We first achieved the use of various alkyl-substituted alkenes in intermolecular [3 + 2] cycloadditions with cyclopropylamine. We also developed a general and efficient strategy for the construction of structurally diverse cyclopentane-based spiro[4.n] skeletons with 1,3-difunctional groups, which broadly exist in natural products and synthetic molecules. Furthermore, we proposed a hydrogen-bond mode between the arylcyclopropylamine and the photocatalyst QXPT-NPh.
Topics & Concepts
CycloadditionCyclopentaneIntermolecular forceChemistryMoleculeAlkylCatalysisHydrogen bondPhotochemistryStereochemistryCombinatorial chemistryOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCO2 Reduction Techniques and Catalysts