Visible Light Activated Benzimidazolequinone Alkoxyamines of 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO)

Patrick Kielty; Benjamin A. Chalmers; Pau Farràs; Dennis A. Smith; Fawaz Aldabbagh

doi:10.1002/ejoc.202101183

Visible Light Activated Benzimidazolequinone Alkoxyamines of 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO)

Patrick Kielty
, Benjamin A. Chalmers
, Pau Farràs
, Dennis A. Smith
, Fawaz Aldabbagh

Sustainable World

University of Galway
Kingston University

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

1 Citation (Scopus)

Abstract

1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO) is a well-known stable 2,3-dihydroisoindoline aminoxyl radical, which is thermally generated (at >100 °C) from literature alkoxyamine derivatives. Herein is the synthesis of visible light activated benzimidazolequinone alkoxyamines of TMIO using oxidative methods and the first room temperature nitroxide-exchange experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) analogues. For the alkoxyamine TMIO-Vis dissociation rate constants are provided using TEMPO and oxygen as radical traps.

Original language	English
Pages (from-to)	6652-6657
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	48
DOIs	https://doi.org/10.1002/ejoc.202101183
Publication status	Published - 28 Dec 2021

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title = "Visible Light Activated Benzimidazolequinone Alkoxyamines of 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO)",

abstract = "1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO) is a well-known stable 2,3-dihydroisoindoline aminoxyl radical, which is thermally generated (at >100 °C) from literature alkoxyamine derivatives. Herein is the synthesis of visible light activated benzimidazolequinone alkoxyamines of TMIO using oxidative methods and the first room temperature nitroxide-exchange experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) analogues. For the alkoxyamine TMIO-Vis dissociation rate constants are provided using TEMPO and oxygen as radical traps.",

author = "Patrick Kielty and Chalmers, \{Benjamin A.\} and Pau Farr{\`a}s and Smith, \{Dennis A.\} and Fawaz Aldabbagh",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

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doi = "10.1002/ejoc.202101183",

language = "English",

volume = "2021",

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TY - JOUR

T1 - Visible Light Activated Benzimidazolequinone Alkoxyamines of 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO)

AU - Kielty, Patrick

AU - Chalmers, Benjamin A.

AU - Farràs, Pau

AU - Smith, Dennis A.

AU - Aldabbagh, Fawaz

PY - 2021/12/28

Y1 - 2021/12/28

N2 - 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO) is a well-known stable 2,3-dihydroisoindoline aminoxyl radical, which is thermally generated (at >100 °C) from literature alkoxyamine derivatives. Herein is the synthesis of visible light activated benzimidazolequinone alkoxyamines of TMIO using oxidative methods and the first room temperature nitroxide-exchange experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) analogues. For the alkoxyamine TMIO-Vis dissociation rate constants are provided using TEMPO and oxygen as radical traps.

AB - 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO) is a well-known stable 2,3-dihydroisoindoline aminoxyl radical, which is thermally generated (at >100 °C) from literature alkoxyamine derivatives. Herein is the synthesis of visible light activated benzimidazolequinone alkoxyamines of TMIO using oxidative methods and the first room temperature nitroxide-exchange experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) analogues. For the alkoxyamine TMIO-Vis dissociation rate constants are provided using TEMPO and oxygen as radical traps.

UR - https://www.scopus.com/pages/publications/85121874409

U2 - 10.1002/ejoc.202101183

DO - 10.1002/ejoc.202101183

M3 - Article

SN - 1434-193X

VL - 2021

SP - 6652

EP - 6657

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 48

ER -

Visible Light Activated Benzimidazolequinone Alkoxyamines of 1,1,3,3-Tetramethylisoindolin-2-yloxyl (TMIO)

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