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

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

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...

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Bibliographic Details
Main Authors: Lisa Marie Kammer, Aliyaah Rahman, Till Opatz
Format: Article
Language:English
Published: MDPI AG 2018-03-01
Series:Molecules
Subjects:
photoredox reactions
Minisci reaction
visible light
free radicals
heterocycles
photocatalysis
Online Access:http://www.mdpi.com/1420-3049/23/4/764
Description
Summary: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.
ISSN:1420-3049

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