Recyclable copper catalysts based on ionic-tagged C 2-symmetric Indabox ligands and their application in asymmetric Henry reactions

Zhi Huai Li; Zhi Ming Zhou; Xiao Yan Hao; Jun Zhang; Xiao Dong; Ying Qiang Liu; Wen Wen Sun; Dan Cao

doi:10.1016/j.apcata.2012.02.044

Recyclable copper catalysts based on ionic-tagged C ₂-symmetric Indabox ligands and their application in asymmetric Henry reactions

Zhi Huai Li, Zhi Ming Zhou^*, Xiao Yan Hao, Jun Zhang, Xiao Dong, Ying Qiang Liu, Wen Wen Sun, Dan Cao

^*Corresponding author for this work

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

20 Citations (Scopus)

Abstract

New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc) ₂· H ₂O were applied to the asymmetric Henry reaction using various aldehydes and CH ₃NO ₂, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

Original language	English
Pages (from-to)	28-34
Number of pages	7
Journal	Applied Catalysis A: General
Volume	425-426
DOIs	https://doi.org/10.1016/j.apcata.2012.02.044
Publication status	Published - 28 May 2012
Externally published	Yes

Keywords

Asymmetric Henry reaction
Catalyst recycled
Imidazolium/pyrrolidinium-tagged Indabox
Theoretical mechanistic study

Access to Document

10.1016/j.apcata.2012.02.044

Cite this

@article{015ee0886591436b819e462cbfb2583c,

title = "Recyclable copper catalysts based on ionic-tagged C 2-symmetric Indabox ligands and their application in asymmetric Henry reactions",

abstract = "New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc) 2· H 2O were applied to the asymmetric Henry reaction using various aldehydes and CH 3NO 2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.",

keywords = "Asymmetric Henry reaction, Catalyst recycled, Imidazolium/pyrrolidinium-tagged Indabox, Theoretical mechanistic study",

author = "Li, {Zhi Huai} and Zhou, {Zhi Ming} and Hao, {Xiao Yan} and Jun Zhang and Xiao Dong and Liu, {Ying Qiang} and Sun, {Wen Wen} and Dan Cao",

year = "2012",

month = may,

day = "28",

doi = "10.1016/j.apcata.2012.02.044",

language = "English",

volume = "425-426",

pages = "28--34",

journal = "Applied Catalysis A: General",

issn = "0926-860X",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Recyclable copper catalysts based on ionic-tagged C 2-symmetric Indabox ligands and their application in asymmetric Henry reactions

AU - Li, Zhi Huai

AU - Zhou, Zhi Ming

AU - Hao, Xiao Yan

AU - Zhang, Jun

AU - Dong, Xiao

AU - Liu, Ying Qiang

AU - Sun, Wen Wen

AU - Cao, Dan

PY - 2012/5/28

Y1 - 2012/5/28

N2 - New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc) 2· H 2O were applied to the asymmetric Henry reaction using various aldehydes and CH 3NO 2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

AB - New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc) 2· H 2O were applied to the asymmetric Henry reaction using various aldehydes and CH 3NO 2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

KW - Asymmetric Henry reaction

KW - Catalyst recycled

KW - Imidazolium/pyrrolidinium-tagged Indabox

KW - Theoretical mechanistic study

UR - http://www.scopus.com/inward/record.url?scp=84862799790&partnerID=8YFLogxK

U2 - 10.1016/j.apcata.2012.02.044

DO - 10.1016/j.apcata.2012.02.044

M3 - Article

AN - SCOPUS:84862799790

SN - 0926-860X

VL - 425-426

SP - 28

EP - 34

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

ER -

Recyclable copper catalysts based on ionic-tagged C ₂-symmetric Indabox ligands and their application in asymmetric Henry reactions

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this