N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates

N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates

An unprecedented N-heterocyclic carbene catalytic reductive β,β-carbon coupling of α,β-nitroalkenes, by using an organic substrate to mimic the one-electron oxidation role of the pyruvate ferredoxin oxidoreductase (PFOR) in living systems, has been developed. The reaction goes through a radical anio...

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Main Authors: Du, Yu, Wang, Yuhuang, Li, Xin, Shao, Yaling, Li, Guohui, Webster, Richard D., Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/107178
http://hdl.handle.net/10220/25333
http://dx.doi.org/10.1021/ol5027415
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1071782019-12-06T22:26:03Z N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates Du, Yu Wang, Yuhuang Li, Xin Shao, Yaling Li, Guohui Webster, Richard D. Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry An unprecedented N-heterocyclic carbene catalytic reductive β,β-carbon coupling of α,β-nitroalkenes, by using an organic substrate to mimic the one-electron oxidation role of the pyruvate ferredoxin oxidoreductase (PFOR) in living systems, has been developed. The reaction goes through a radical anion intermediate generated under a catalytic redox process. For the first time, the presence of radical anion intermediate in NHC organocatalysis is observed and clearly verified. 2015-04-07T08:33:27Z 2019-12-06T22:26:03Z 2015-04-07T08:33:27Z 2019-12-06T22:26:03Z 2014 2014 Journal Article Du, Y., Wang, Y., Li, X., Shao, Y., Li, G., Webster, R. D., et al. (2014). N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates. Organic letters, 16(21), 5678-5681. https://hdl.handle.net/10356/107178 http://hdl.handle.net/10220/25333 http://dx.doi.org/10.1021/ol5027415 184169 en Organic letters © 2014 American Chemical Society.
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
Du, Yu
Wang, Yuhuang
Li, Xin
Shao, Yaling
Li, Guohui
Webster, Richard D.
Chi, Robin Yonggui
N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
description An unprecedented N-heterocyclic carbene catalytic reductive β,β-carbon coupling of α,β-nitroalkenes, by using an organic substrate to mimic the one-electron oxidation role of the pyruvate ferredoxin oxidoreductase (PFOR) in living systems, has been developed. The reaction goes through a radical anion intermediate generated under a catalytic redox process. For the first time, the presence of radical anion intermediate in NHC organocatalysis is observed and clearly verified.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Du, Yu
Wang, Yuhuang
Li, Xin
Shao, Yaling
Li, Guohui
Webster, Richard D.
Chi, Robin Yonggui
format Article
author Du, Yu
Wang, Yuhuang
Li, Xin
Shao, Yaling
Li, Guohui
Webster, Richard D.
Chi, Robin Yonggui
author_sort Du, Yu
title N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
title_short N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
title_full N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
title_fullStr N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
title_full_unstemmed N-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
title_sort n-heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates
publishDate 2015
url https://hdl.handle.net/10356/107178
http://hdl.handle.net/10220/25333
http://dx.doi.org/10.1021/ol5027415
_version_ 1681049440713965568

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