Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation

Pang Fei Teng; Chui Shan Tsang; Ho Lun Yeung; Wing Leung Wong; Wing Tak Wong; Hoi Lun Kwong

doi:10.1016/j.jorganchem.2006.06.050

Syntheses of C₁-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation

Pang Fei Teng, Chui Shan Tsang, Ho Lun Yeung, Wing Leung Wong, Wing Tak Wong, Hoi Lun Kwong

Research output: Journal article publication › Journal article › Academic research › peer-review

21 Citations (Scopus)

Abstract

New chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate.

Original language	English
Pages (from-to)	5676-5684
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	691
Issue number	26
DOIs	https://doi.org/10.1016/j.jorganchem.2006.06.050
Publication status	Published - 15 Dec 2006
Externally published	Yes

Keywords

Allylic Substitution
Copper
Cyclopropanation
Palladium
Pyridyl

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2006.06.050

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Teng, P. F., Tsang, C. S., Yeung, H. L., Wong, W. L., Wong, W. T., & Kwong, H. L. (2006). Syntheses of C₁-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation. Journal of Organometallic Chemistry, 691(26), 5676-5684. https://doi.org/10.1016/j.jorganchem.2006.06.050

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title = "Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation",

abstract = "New chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kr{\"o}hnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate.",

keywords = "Allylic Substitution, Copper, Cyclopropanation, Palladium, Pyridyl",

author = "Teng, {Pang Fei} and Tsang, {Chui Shan} and Yeung, {Ho Lun} and Wong, {Wing Leung} and Wong, {Wing Tak} and Kwong, {Hoi Lun}",

year = "2006",

month = dec,

day = "15",

doi = "10.1016/j.jorganchem.2006.06.050",

language = "English",

volume = "691",

pages = "5676--5684",

journal = "Journal of Organometallic Chemistry",

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Teng, PF, Tsang, CS, Yeung, HL, Wong, WL , Wong, WT & Kwong, HL 2006, 'Syntheses of C₁-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation', Journal of Organometallic Chemistry, vol. 691, no. 26, pp. 5676-5684. https://doi.org/10.1016/j.jorganchem.2006.06.050

Syntheses of C₁-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation. / Teng, Pang Fei; Tsang, Chui Shan; Yeung, Ho Lun et al.

In: Journal of Organometallic Chemistry, Vol. 691, No. 26, 15.12.2006, p. 5676-5684.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation

AU - Teng, Pang Fei

AU - Tsang, Chui Shan

AU - Yeung, Ho Lun

AU - Wong, Wing Leung

AU - Wong, Wing Tak

AU - Kwong, Hoi Lun

PY - 2006/12/15

Y1 - 2006/12/15

N2 - New chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate.

AB - New chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate.

KW - Allylic Substitution

KW - Copper

KW - Cyclopropanation

KW - Palladium

KW - Pyridyl

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U2 - 10.1016/j.jorganchem.2006.06.050

DO - 10.1016/j.jorganchem.2006.06.050

M3 - Journal article

VL - 691

SP - 5676

EP - 5684

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 26

ER -

Teng PF, Tsang CS, Yeung HL, Wong WL , Wong WT, Kwong HL. Syntheses of C₁-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation. Journal of Organometallic Chemistry. 2006 Dec 15;691(26):5676-5684. https://doi.org/10.1016/j.jorganchem.2006.06.050