Visible-Light Organophotoredox-Mediated [3+2] Cycloaddition of Arylcyclopropylamine with Structurally Diverse Olefins for the Construction of Cyclopentylamines and Spiro[4.n] Skeletons

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.

Automated summary

In this study, we developed a visible-light-mediated [3 + 2] cycloaddition reaction by using QXPT-NPh as an efficient organic photoredox catalyst, enabling the reaction between arylcyclopropylamine and structurally diverse olefins. This method provides a general and efficient strategy for constructing cyclopentane-based spiro[4.n] skeletons with 1,3-difunctional groups, which are widely present in natural products and synthetic molecules. Additionally, we proposed a hydrogen-bond mode between arylcyclopropylamine and the photocatalyst QXPT-NPh.