N-heterocyclic carbene-catalyzed δ-Carbon LUMO activation of unsaturated aldehydes

Tingshun Zhu; Chengli Mou; Baosheng Li; Marie Smetankova; Bao An Song; Yonggui Robin Chi

doi:10.1021/jacs.5b02219

N-heterocyclic carbene-catalyzed δ-Carbon LUMO activation of unsaturated aldehydes

Tingshun Zhu, Chengli Mou, Baosheng Li, Marie Smetankova, Bao An Song^*, Yonggui Robin Chi

^*Corresponding author for this work

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

100 Citations (Scopus)

Abstract

An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.

Original language	English
Pages (from-to)	5658-5661
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	17
DOIs	https://doi.org/10.1021/jacs.5b02219
Publication status	Published - May 6 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.",

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AU - Mou, Chengli

AU - Li, Baosheng

AU - Smetankova, Marie

AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2015/5/6

Y1 - 2015/5/6

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AB - An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.

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N-heterocyclic carbene-catalyzed δ-Carbon LUMO activation of unsaturated aldehydes

Abstract

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ASJC Scopus Subject Areas

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