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Harnessing Energy-Transfer in N-Centered Radical-Mediated Synthesis of Pyrrolidines

Journal article
Authors Peter Fodran
Carl Johan Wallentin
Published in European Journal of Organic Chemistry
Volume 2020
Issue 22
Pages 3213-3218
ISSN 1434-193X
Publication year 2020
Published at Department of Chemistry and Molecular Biology
Pages 3213-3218
Language en
Links dx.doi.org/10.1002/ejoc.202000537
https://gup.ub.gu.se/file/208145
Keywords ATRA, ATRC, Energy-transfer, Nitrogen heterocycles, Photocatalysis, atom-transfer, alkenes, derivatives, photochemistry, cycloaddition, rearrangement, cyclization, catalysis, iodides, alkynes, Chemistry
Subject categories Organic Chemistry

Abstract

Atom transfer radical addition (ATRA), cyclization (ATRC), and polymerization (ATRP) are valuable synthetic methods for the functionalization of olefins. With the advent of photoredox catalysis, visible-light became a popular tool for the initiation of these reactions. We have developed a protocol that enables easy access to distally functionalized pyrrolidines employing blue-light mediated atom transfer radical [3+2] cyclization. The reaction is scalable, proceeds at very mild conditions. tolerates various functional groups, and provides the corresponding products in good to excellent yields. If rigid olefins are utilized as the reaction partners, the products can be isolated as single diastereomers. The mechanistic investigations provide strong support for an energy-transfer mechanism.

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