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 Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

25 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. © 2006 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	5676-5684
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

Research Keywords

Allylic Substitution
Copper
Cyclopropanation
Palladium
Pyridyl

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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

@article{af16987ae9e04f868d116393c4a36ee4,

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. {\textcopyright} 2006 Elsevier B.V. All rights reserved.",

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

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

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",

issn = "0022-328X",

publisher = "Elsevier B.V.",

number = "26",

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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, 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 Publications and Reviews › RGC 21 - Publication in refereed journal › 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. © 2006 Elsevier B.V. All rights reserved.

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. © 2006 Elsevier B.V. All rights reserved.

KW - Allylic Substitution

KW - Copper

KW - Cyclopropanation

KW - Palladium

KW - Pyridyl

UR - https://www.scopus.com/pages/publications/33751342266

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-33751342266&origin=recordpage

U2 - 10.1016/j.jorganchem.2006.06.050

DO - 10.1016/j.jorganchem.2006.06.050

M3 - RGC 21 - Publication in refereed journal

SN - 0022-328X

VL - 691

SP - 5676

EP - 5684

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

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. 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

Abstract

Research Keywords

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