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Molecules 2018, 23(4), 764; https://doi.org/10.3390/molecules23040764

A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters

Institute of Organic Chemistry, Johannes Gutenberg-University, 55128 Mainz, Germany
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Received: 9 March 2018 / Revised: 21 March 2018 / Accepted: 22 March 2018 / Published: 27 March 2018
(This article belongs to the Special Issue Radical Chemistry)
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Abstract

A visible light-promoted protocol for the redox-neutral coupling of N-hydroxyphthalimide esters with different N-heterocyclic compounds is described. The reaction proceeds through an alkyl radical intermediate generated by reductive decarboxylation of N-hydroxyphthalimide esters. In contrast to the original Minisci protocol, polyalkylation can largely be avoided. Mechanistic investigations revealed a radical chain mechanism which in some cases can proceed even if no photocatalyst is added. This valuable and functional group-tolerant reaction produces substituted heterocycles in moderate to excellent yield. The use of inexpensive starting materials and LEDs as the light source are key features of this C–C bond formation. View Full-Text
Keywords: photoredox reactions; Minisci reaction; visible light; free radicals; heterocycles; photocatalysis photoredox reactions; Minisci reaction; visible light; free radicals; heterocycles; photocatalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kammer, L.M.; Rahman, A.; Opatz, T. A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters. Molecules 2018, 23, 764.

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