Chiral C1-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene

Chi Tung Yeung; Wing Sze Lee; Chui Shan Tsang; Shek Man Yiu; Wing Tak Wong; Wai Yeung WONG; Hoi Lun Kwong

doi:10.1016/j.poly.2010.01.017

Chiral C₁-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene

Chi Tung Yeung, Wing Sze Lee, Chui Shan Tsang, Shek Man Yiu, Wing Tak Wong, Wai Yeung WONG, Hoi Lun Kwong^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

24 Citations (Scopus)

Abstract

Three new optically pure C₁-terpyridine ligands (L1-3) were prepared and the copper(II) complexes, of formula [Cu(L)Cl₂], the rhodium(III) complexes, of formula [Rh(L)Cl₃], and the ruthenium(II) complexes, of formula cis- or trans-[Ru(L)(X)Cl₂] (X = DMSO or CO), were synthesized. Structures of a chiral C₁-ligand, a copper complex, a rhodium complex and a ruthenium DMSO complex were analysed using X-ray crystal structure analysis. The copper, rhodium and ruthenium complexes were shown to be precursors of catalysts for cyclopropanation. Reaction of [Cu(L)Cl₂], [Rh(L)Cl₃] or cis- or trans-[Ru(L)(X)Cl₂] with AgOTf converted the complex to catalyst, which in the case of trans-[Ru(L)(CO)Cl₂] gave enantioselectivities of up to 67% ee for the cis-isomers of styrene cyclopropanes with t-butyl diazoacetate. Comparisons with C₂-analog of copper, rhodium and ruthenium catalysts were made.

Original language	English
Pages (from-to)	1497-1507
Number of pages	11
Journal	Polyhedron
Volume	29
Issue number	5
DOIs	https://doi.org/10.1016/j.poly.2010.01.017
Publication status	Published - 30 Mar 2010

Scopus Subject Areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

User-Defined Keywords

Asymmetric catalysis
Chiral terpyridine
Copper
Metal-catalyzed cyclopropanation
Rhodium
Ruthenium

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Yeung, C. T., Lee, W. S., Tsang, C. S., Yiu, S. M., Wong, W. T., WONG, W. Y., & Kwong, H. L. (2010). Chiral C₁-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene. Polyhedron, 29(5), 1497-1507. https://doi.org/10.1016/j.poly.2010.01.017

@article{1f573efcfc164a6bae6f8ae583953d55,

title = "Chiral C1-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene",

abstract = "Three new optically pure C1-terpyridine ligands (L1-3) were prepared and the copper(II) complexes, of formula [Cu(L)Cl2], the rhodium(III) complexes, of formula [Rh(L)Cl3], and the ruthenium(II) complexes, of formula cis- or trans-[Ru(L)(X)Cl2] (X = DMSO or CO), were synthesized. Structures of a chiral C1-ligand, a copper complex, a rhodium complex and a ruthenium DMSO complex were analysed using X-ray crystal structure analysis. The copper, rhodium and ruthenium complexes were shown to be precursors of catalysts for cyclopropanation. Reaction of [Cu(L)Cl2], [Rh(L)Cl3] or cis- or trans-[Ru(L)(X)Cl2] with AgOTf converted the complex to catalyst, which in the case of trans-[Ru(L)(CO)Cl2] gave enantioselectivities of up to 67% ee for the cis-isomers of styrene cyclopropanes with t-butyl diazoacetate. Comparisons with C2-analog of copper, rhodium and ruthenium catalysts were made.",

keywords = "Asymmetric catalysis, Chiral terpyridine, Copper, Metal-catalyzed cyclopropanation, Rhodium, Ruthenium",

author = "Yeung, {Chi Tung} and Lee, {Wing Sze} and Tsang, {Chui Shan} and Yiu, {Shek Man} and Wong, {Wing Tak} and WONG, {Wai Yeung} and Kwong, {Hoi Lun}",

note = "Funding Information: Financial support for this research from the Hong Kong Research Grants Council the Area of Excellence Scheme established under the University Grants Committee of the Hong Kong SAR, China (Project No. AoE/P-10/01 ) and GRF grant (CityU 101108). are gratefully acknowledged.",

year = "2010",

month = mar,

day = "30",

doi = "10.1016/j.poly.2010.01.017",

language = "English",

volume = "29",

pages = "1497--1507",

journal = "Polyhedron",

issn = "0277-5387",

publisher = "Elsevier Ltd.",

number = "5",

}

Yeung, CT, Lee, WS, Tsang, CS, Yiu, SM, Wong, WT, WONG, WY & Kwong, HL 2010, 'Chiral C₁-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene', Polyhedron, vol. 29, no. 5, pp. 1497-1507. https://doi.org/10.1016/j.poly.2010.01.017

Chiral C₁-symmetric 2,2′:6′,2′′-terpyridine ligands: Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene. / Yeung, Chi Tung; Lee, Wing Sze; Tsang, Chui Shan et al.
In: Polyhedron, Vol. 29, No. 5, 30.03.2010, p. 1497-1507.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Chiral C1-symmetric 2,2′:6′,2′′-terpyridine ligands

T2 - Synthesis, characterization, complexation with copper(II), rhodium(III) and ruthenium(II) ions and use of the complexes in catalytic cyclopropanation of styrene

AU - Yeung, Chi Tung

AU - Lee, Wing Sze

AU - Tsang, Chui Shan

AU - Yiu, Shek Man

AU - Wong, Wing Tak

AU - WONG, Wai Yeung

AU - Kwong, Hoi Lun

N1 - Funding Information: Financial support for this research from the Hong Kong Research Grants Council the Area of Excellence Scheme established under the University Grants Committee of the Hong Kong SAR, China (Project No. AoE/P-10/01 ) and GRF grant (CityU 101108). are gratefully acknowledged.

PY - 2010/3/30

Y1 - 2010/3/30

N2 - Three new optically pure C1-terpyridine ligands (L1-3) were prepared and the copper(II) complexes, of formula [Cu(L)Cl2], the rhodium(III) complexes, of formula [Rh(L)Cl3], and the ruthenium(II) complexes, of formula cis- or trans-[Ru(L)(X)Cl2] (X = DMSO or CO), were synthesized. Structures of a chiral C1-ligand, a copper complex, a rhodium complex and a ruthenium DMSO complex were analysed using X-ray crystal structure analysis. The copper, rhodium and ruthenium complexes were shown to be precursors of catalysts for cyclopropanation. Reaction of [Cu(L)Cl2], [Rh(L)Cl3] or cis- or trans-[Ru(L)(X)Cl2] with AgOTf converted the complex to catalyst, which in the case of trans-[Ru(L)(CO)Cl2] gave enantioselectivities of up to 67% ee for the cis-isomers of styrene cyclopropanes with t-butyl diazoacetate. Comparisons with C2-analog of copper, rhodium and ruthenium catalysts were made.

AB - Three new optically pure C1-terpyridine ligands (L1-3) were prepared and the copper(II) complexes, of formula [Cu(L)Cl2], the rhodium(III) complexes, of formula [Rh(L)Cl3], and the ruthenium(II) complexes, of formula cis- or trans-[Ru(L)(X)Cl2] (X = DMSO or CO), were synthesized. Structures of a chiral C1-ligand, a copper complex, a rhodium complex and a ruthenium DMSO complex were analysed using X-ray crystal structure analysis. The copper, rhodium and ruthenium complexes were shown to be precursors of catalysts for cyclopropanation. Reaction of [Cu(L)Cl2], [Rh(L)Cl3] or cis- or trans-[Ru(L)(X)Cl2] with AgOTf converted the complex to catalyst, which in the case of trans-[Ru(L)(CO)Cl2] gave enantioselectivities of up to 67% ee for the cis-isomers of styrene cyclopropanes with t-butyl diazoacetate. Comparisons with C2-analog of copper, rhodium and ruthenium catalysts were made.

KW - Asymmetric catalysis

KW - Chiral terpyridine

KW - Copper

KW - Metal-catalyzed cyclopropanation

KW - Rhodium

KW - Ruthenium

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U2 - 10.1016/j.poly.2010.01.017

DO - 10.1016/j.poly.2010.01.017

M3 - Journal article

AN - SCOPUS:77649271172

SN - 0277-5387

VL - 29

SP - 1497

EP - 1507

JO - Polyhedron

JF - Polyhedron

IS - 5

ER -