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

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.

Autoren

Lisa Kammer
Aliyaah Rahman
Till Opatz

DOI

10.3390/molecules23040764

eISSN

1420-3049

Ausgabe der Veröffentlichung

4

Zeitschrift

Molecules

Sprache

en

Online publication date

2018

Paginierung

764 - 764

Status

Published online

Herausgeber

MDPI AG

Herausgeber URL

http://dx.doi.org/10.3390/molecules23040764

Datum der Datenerfassung

2024

Titel

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

Ausgabe der Zeitschrift

23

Datenquelle: Crossref

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.

Addresses

Institute of Organic Chemistry, Johannes Gutenberg-University, 55128 Mainz, Germany. kammer@uni-mainz.de.

Autoren

Lisa Marie Kammer
Aliyaah Rahman
Till Opatz

DOI

10.3390/molecules23040764

eISSN

1420-3049

Externe Identifier

PubMed Identifier: 29584642
PubMed Central ID: PMC6017455

Funding acknowledgements

Studienstiftung des Deutschen Volkes: n/a
University of Mainz: LESSING

Open access

true

ISSN

1420-3049

Ausgabe der Veröffentlichung

4

Zeitschrift

Molecules (Basel, Switzerland)

Schlüsselwörter

Phthalimides
Esters
Heterocyclic Compounds
Molecular Structure
Decarboxylation
Catalysis
Light
Photochemical Processes

Sprache

eng

Medium

Electronic

Online publication date

2018

Open access status

Open Access

Paginierung

E764

Datum der Veröffentlichung

2018

Status

Published

Publisher licence

CC BY

Datum der Datenerfassung

2018

Titel

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

Sub types

research-article
Journal Article

Ausgabe der Zeitschrift

23

Files

https://www.mdpi.com/1420-3049/23/4/764/pdf?version=1525345352 https://europepmc.org/articles/PMC6017455?pdf=render

Datenquelle: Europe PubMed Central

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.

Date of acceptance

2018

Autoren

Lisa Marie Kammer
Aliyaah Rahman
Till Opatz

Autoren-URL

https://www.ncbi.nlm.nih.gov/pubmed/29584642

DOI

10.3390/molecules23040764

eISSN

1420-3049

Externe Identifier

PubMed Central ID: PMC6017455

Ausgabe der Veröffentlichung

4

Zeitschrift

Molecules

Schlüsselwörter

Minisci reaction
free radicals
heterocycles
photocatalysis
photoredox reactions
visible light
Catalysis
Decarboxylation
Esters
Heterocyclic Compounds
Light
Molecular Structure
Photochemical Processes
Phthalimides

Sprache

eng

Country

Switzerland

PII

molecules23040764

Datum der Veröffentlichung

2018

Status

Published online

Datum, an dem der Datensatz öffentlich gemacht wurde

2018

Titel

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

Sub types

Journal Article

Ausgabe der Zeitschrift

23

Datenquelle: PubMed

Author's licence

CC-BY

Autoren

Lisa Marie Kammer
Aliyaah Rahman
Till Opatz

Hosting institution

Universitätsbibliothek Mainz

Sammlungen

JGU-Publikationen

Resource version

Published version

DOI

10.3390/molecules23040764

Funding acknowledgements

DFG, Open Access-Publizieren Universität Mainz / Universitätsmedizin

File(s) embargoed

false

Open access

true

ISSN

1420-3049

Ausgabe der Veröffentlichung

4

Zeitschrift

Molecules

Schlüsselwörter

540 Chemie
540 Chemistry and allied sciences

Sprache

eng

Open access status

Open Access

Paginierung

Art. 764

Datum der Veröffentlichung

2018

Public URL

https://openscience.ub.uni-mainz.de/handle/20.500.12030/377

Herausgeber

MDPI

Herausgeber URL

http://dx.doi.org/10.3390/molecules23040764

Datum der Datenerfassung

2018

Datum, an dem der Datensatz öffentlich gemacht wurde

2018

Zugang

Public

Titel

A visible light-driven Minisci-type reaction with N-hydroxyphthalimide esters

Ausgabe der Zeitschrift

23

Files

58101.pdf

Datenquelle: OPENSCIENCE.UB

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

Files

Files

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