Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

Weiguo Jia; Dandan Li; Yuanchen Dai; Hui Zhang; Liqin Yan; Enhong Sheng; Yun Wei; Xiaolong Mu; Kuo-Wei Huang

doi:10.1039/c4ob01027b

Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

Weiguo Jia, Dandan Li, Yuanchen Dai, Hui Zhang, Liqin Yan, Enhong Sheng, Yun Wei, Xiaolong Mu, Kuo-Wei Huang

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

28 Scopus citations

Abstract

Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2] (3) (Dm-Pybox = 2,6-bis[4′,4′- dimethyloxazolin-2′-yl]pyridine) were obtained by reactions of CuX 2 (X = Cl, Br) with DMOX and Dm-Pybox ligands, respectively. The molecular structures of 1, 2 and 3 have been determined by single-crystal X-ray diffraction analyses. The complexes 2 and 3 are efficient in catalyzing α-amination of ketones and esters through α-bromo carbonyl intermediate. The procedures are environmentally benign methods using molecular oxygen as an oxidant with water as the only byproduct. This journal is © the Partner Organisations 2014.

Original language	English (US)
Pages (from-to)	5509-5516
Number of pages	8
Journal	Organic & Biomolecular Chemistry
Volume	12
Issue number	29
DOIs	https://doi.org/10.1039/c4ob01027b
State	Published - 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the National Nature Science Foundation of China (21102004), and the Natural Science Foundation of the Anhui Higher Education Institutions of China (KJ2011A146), and the Project-sponsored by SRF for ROCS, SEM. K.-W. Huang acknowledges financial support from KAUST. We also thank Dr Richmond Lee for English polishing.

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1039/c4ob01027b

Cite this

@article{1367bd23ceff484da541ac6892d3f7f5,

title = "Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines",

abstract = "Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2] (3) (Dm-Pybox = 2,6-bis[4′,4′- dimethyloxazolin-2′-yl]pyridine) were obtained by reactions of CuX 2 (X = Cl, Br) with DMOX and Dm-Pybox ligands, respectively. The molecular structures of 1, 2 and 3 have been determined by single-crystal X-ray diffraction analyses. The complexes 2 and 3 are efficient in catalyzing α-amination of ketones and esters through α-bromo carbonyl intermediate. The procedures are environmentally benign methods using molecular oxygen as an oxidant with water as the only byproduct. This journal is {\textcopyright} the Partner Organisations 2014.",

author = "Weiguo Jia and Dandan Li and Yuanchen Dai and Hui Zhang and Liqin Yan and Enhong Sheng and Yun Wei and Xiaolong Mu and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Nature Science Foundation of China (21102004), and the Natural Science Foundation of the Anhui Higher Education Institutions of China (KJ2011A146), and the Project-sponsored by SRF for ROCS, SEM. K.-W. Huang acknowledges financial support from KAUST. We also thank Dr Richmond Lee for English polishing.",

year = "2014",

doi = "10.1039/c4ob01027b",

language = "English (US)",

volume = "12",

pages = "5509--5516",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "29",

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TY - JOUR

T1 - Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

AU - Jia, Weiguo

AU - Li, Dandan

AU - Dai, Yuanchen

AU - Zhang, Hui

AU - Yan, Liqin

AU - Sheng, Enhong

AU - Wei, Yun

AU - Mu, Xiaolong

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Nature Science Foundation of China (21102004), and the Natural Science Foundation of the Anhui Higher Education Institutions of China (KJ2011A146), and the Project-sponsored by SRF for ROCS, SEM. K.-W. Huang acknowledges financial support from KAUST. We also thank Dr Richmond Lee for English polishing.

PY - 2014

Y1 - 2014

N2 - Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2] (3) (Dm-Pybox = 2,6-bis[4′,4′- dimethyloxazolin-2′-yl]pyridine) were obtained by reactions of CuX 2 (X = Cl, Br) with DMOX and Dm-Pybox ligands, respectively. The molecular structures of 1, 2 and 3 have been determined by single-crystal X-ray diffraction analyses. The complexes 2 and 3 are efficient in catalyzing α-amination of ketones and esters through α-bromo carbonyl intermediate. The procedures are environmentally benign methods using molecular oxygen as an oxidant with water as the only byproduct. This journal is © the Partner Organisations 2014.

AB - Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2] (3) (Dm-Pybox = 2,6-bis[4′,4′- dimethyloxazolin-2′-yl]pyridine) were obtained by reactions of CuX 2 (X = Cl, Br) with DMOX and Dm-Pybox ligands, respectively. The molecular structures of 1, 2 and 3 have been determined by single-crystal X-ray diffraction analyses. The complexes 2 and 3 are efficient in catalyzing α-amination of ketones and esters through α-bromo carbonyl intermediate. The procedures are environmentally benign methods using molecular oxygen as an oxidant with water as the only byproduct. This journal is © the Partner Organisations 2014.

UR - http://hdl.handle.net/10754/563220

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U2 - 10.1039/c4ob01027b

DO - 10.1039/c4ob01027b

M3 - Article

SN - 1477-0520

VL - 12

SP - 5509

EP - 5516

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 29

ER -

Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

Abstract

Bibliographical note

ASJC Scopus subject areas

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CCDC 981179: Experimental Crystal Structure Determination : dibromo-(4,4,4',4'-tetramethyl-4,4',5,5'-tetrahydro-2,2'-bi-1,3-oxazole)-copper(ii)

CCDC 973034: Experimental Crystal Structure Determination : bis(mu~2~-chloro)-dichloro-bis(4,4,4',4'-tetramethyl-4,4',5,5'-tetrahydro-2,2'-bi-1,3-oxazole)-di-copper

CCDC 973033: Experimental Crystal Structure Determination : (2,6-bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine)-dibromo-copper(ii)

Cite this

Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 981179: Experimental Crystal Structure Determination : dibromo-(4,4,4',4'-tetramethyl-4,4',5,5'-tetrahydro-2,2'-bi-1,3-oxazole)-copper(ii)

CCDC 973034: Experimental Crystal Structure Determination : bis(mu~2~-chloro)-dichloro-bis(4,4,4',4'-tetramethyl-4,4',5,5'-tetrahydro-2,2'-bi-1,3-oxazole)-di-copper

CCDC 973033: Experimental Crystal Structure Determination : (2,6-bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine)-dibromo-copper(ii)

Cite this