Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction

Qiong Ji Yao; Duc Thinh Khong; Qi Gao; Zaher M.A. Judeh

doi:10.1055/s-0033-1341125

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction

Qiong Ji Yao, Duc Thinh Khong, Qi Gao, Zaher M.A. Judeh^*

^*Corresponding author for this work

Nanyang Technological University

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

6 Citations (Scopus)

Abstract

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C ₁-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C ₁-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions.

Original language	English
Article number	SS-2013-N0722-OP
Pages (from-to)	1793-1801
Number of pages	9
Journal	Synthesis
Volume	46
Issue number	13
DOIs	https://doi.org/10.1055/s-0033-1341125
Publication status	Published - Jul 2014
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

biisoquinoline
C-C bond formation
catalyst design
Henry reaction
Proton Sponge

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abstract = "Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C 1-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C 1-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions.",

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T1 - Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction

AU - Yao, Qiong Ji

AU - Khong, Duc Thinh

AU - Gao, Qi

AU - Judeh, Zaher M.A.

PY - 2014/7

Y1 - 2014/7

N2 - Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C 1-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C 1-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions.

AB - Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C 1-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C 1-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions.

KW - biisoquinoline

KW - C-C bond formation

KW - catalyst design

KW - Henry reaction

KW - Proton Sponge

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ER -

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction

Abstract

ASJC Scopus Subject Areas

Keywords

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