Organic dye-photocatalyzed acylnitroso ene reaction

Rose bengal, an inexpensive and readily available organic dye, is demonstrated to be a photoredox catalyst for the formation of transient acylnitroso intermediates under visible light irradiation. This method is operationally simple and uses air as the terminal oxidant. Reactions of acylnitroso with...

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Main Authors: Teo, Yew Chin, Pan, Yuanhang, Tan, Choon Hong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
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Online Access:https://hdl.handle.net/10356/101700
http://hdl.handle.net/10220/19790
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1017002020-03-07T12:34:53Z Organic dye-photocatalyzed acylnitroso ene reaction Teo, Yew Chin Pan, Yuanhang Tan, Choon Hong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry Rose bengal, an inexpensive and readily available organic dye, is demonstrated to be a photoredox catalyst for the formation of transient acylnitroso intermediates under visible light irradiation. This method is operationally simple and uses air as the terminal oxidant. Reactions of acylnitroso with a range of functionalized alkenes give intermolecular acylnitroso ene products in moderate to good yields. This is an environmentally friendly allylic amination methodology that avoids the use of metal catalysts and stoichiometric amount of oxidants. A plausible reaction mechanism is proposed on the basis of singlet oxygen and fluorescence quenching studies. 2014-06-16T03:57:07Z 2019-12-06T20:43:00Z 2014-06-16T03:57:07Z 2019-12-06T20:43:00Z 2013 2013 Journal Article Teo, Y. C., Pan, Y., & Tan, C. H. (2013). Organic Dye-Photocatalyzed Acylnitroso Ene Reaction. ChemCatChem, 5(1), 235-240. 1867-3880 https://hdl.handle.net/10356/101700 http://hdl.handle.net/10220/19790 10.1002/cctc.201200435 en Chemcatchem © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Teo, Yew Chin
Pan, Yuanhang
Tan, Choon Hong
Organic dye-photocatalyzed acylnitroso ene reaction
description Rose bengal, an inexpensive and readily available organic dye, is demonstrated to be a photoredox catalyst for the formation of transient acylnitroso intermediates under visible light irradiation. This method is operationally simple and uses air as the terminal oxidant. Reactions of acylnitroso with a range of functionalized alkenes give intermolecular acylnitroso ene products in moderate to good yields. This is an environmentally friendly allylic amination methodology that avoids the use of metal catalysts and stoichiometric amount of oxidants. A plausible reaction mechanism is proposed on the basis of singlet oxygen and fluorescence quenching studies.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Teo, Yew Chin
Pan, Yuanhang
Tan, Choon Hong
format Article
author Teo, Yew Chin
Pan, Yuanhang
Tan, Choon Hong
author_sort Teo, Yew Chin
title Organic dye-photocatalyzed acylnitroso ene reaction
title_short Organic dye-photocatalyzed acylnitroso ene reaction
title_full Organic dye-photocatalyzed acylnitroso ene reaction
title_fullStr Organic dye-photocatalyzed acylnitroso ene reaction
title_full_unstemmed Organic dye-photocatalyzed acylnitroso ene reaction
title_sort organic dye-photocatalyzed acylnitroso ene reaction
publishDate 2014
url https://hdl.handle.net/10356/101700
http://hdl.handle.net/10220/19790
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