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

Yu Du; Yuhuang Wang; Xin Li; Yaling Shao; Guohui Li; Richard D. Webster; Yonggui Robin Chi

doi:10.1021/ol5027415

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

Yu Du, Yuhuang Wang, Xin Li, Yaling Shao, Guohui Li^*, Richard D. Webster, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

77 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	5678-5681
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol5027415
Publication status	Published - Nov 7 2014
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

abstract = "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.",

author = "Yu Du and Yuhuang Wang and Xin Li and Yaling Shao and Guohui Li and Webster, \{Richard D.\} and Chi, \{Yonggui Robin\}",

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T1 - N -heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates

AU - Du, Yu

AU - Wang, Yuhuang

AU - Li, Xin

AU - Shao, Yaling

AU - Li, Guohui

AU - Webster, Richard D.

AU - Chi, Yonggui Robin

PY - 2014/11/7

Y1 - 2014/11/7

N2 - 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.

AB - 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.

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SP - 5678

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

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ASJC Scopus Subject Areas

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