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Visible-Light-Accelerated Copper-Catalyzed [3 + 2] Cycloaddition of N-Tosylcyclopropylamines with Alkynes/Alkenes

Manoj Kumar, Shalini Verma, Vivek Mishra, Oliver Reiser* and Akhilesh K. Verma*

*Universität Regensburg, Universitätsstr, 93053 Regensburg, Germany; University of Delhi, Delhi 110007, India, Email: oliver.reiserchemie.uni-regensburg.de, avermaacbr.du.ac.in

M. Kumar, S. Verma, V. Mishra, O. Reiser, A. K. Verma J. Org. Chem., 2022, 87, 6263-6272.

DOI: 10.1021/acs.joc.2c00491


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Abstract

Copper-catalyzed [3 + 2] cycloadditions of N-tosylcyclopropylamine with alkynes and alkenes under visible light irradiation provide diversified aminated cyclopentene and cyclopentane derivatives being relevant for drug synthesis. The protocol is operationally simple, economically affordable, and compatible with a range of functionalities.

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proposed mechanism



Key Words

cyclopentanes, cyclopentenes, alkylamines, allylamines, photochemistry


ID: J42-Y2022