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

Handle URI:
http://hdl.handle.net/10754/563220
Title:
Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines
Authors:
Jia, Weiguo; Li, Dandan; Dai, Yuanchen; Zhang, Hui; Yan, Liqin; Sheng, Enhong; Wei, Yun; Mu, Xiaolong; Huang, Kuo-Wei ( 0000-0003-1900-2658 )
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Organic & Biomolecular Chemistry
Issue Date:
2014
DOI:
10.1039/c4ob01027b
Type:
Article
ISSN:
14770520
Sponsors:
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.
Is Supplemented By:
Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973033: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj5d; DOI:10.5517/cc11nj5d; HANDLE:http://hdl.handle.net/10754/624286; Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973034: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj6f; DOI:10.5517/cc11nj6f; HANDLE:http://hdl.handle.net/10754/624287; Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 978999: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11vqm7; DOI:10.5517/cc11vqm7; HANDLE:http://hdl.handle.net/10754/624301; Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 981179: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11xzyw; DOI:10.5517/cc11xzyw; HANDLE:http://hdl.handle.net/10754/624303
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorJia, Weiguoen
dc.contributor.authorLi, Dandanen
dc.contributor.authorDai, Yuanchenen
dc.contributor.authorZhang, Huien
dc.contributor.authorYan, Liqinen
dc.contributor.authorSheng, Enhongen
dc.contributor.authorWei, Yunen
dc.contributor.authorMu, Xiaolongen
dc.contributor.authorHuang, Kuo-Weien
dc.date.accessioned2015-08-03T11:43:28Zen
dc.date.available2015-08-03T11:43:28Zen
dc.date.issued2014en
dc.identifier.issn14770520en
dc.identifier.doi10.1039/c4ob01027ben
dc.identifier.urihttp://hdl.handle.net/10754/563220en
dc.description.abstractBinuclear 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.en
dc.description.sponsorshipThis 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.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleSynthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized aminesen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalOrganic & Biomolecular Chemistryen
dc.contributor.institutionKey Laboratory of Functional Molecular Solids, Anhui Normal University, Ministry of Education, Wuhu 241000, Chinaen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByJia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973033: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj5den
dc.relation.isSupplementedByDOI:10.5517/cc11nj5den
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624286en
dc.relation.isSupplementedByJia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973034: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj6fen
dc.relation.isSupplementedByDOI:10.5517/cc11nj6fen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624287en
dc.relation.isSupplementedByJia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 978999: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11vqm7en
dc.relation.isSupplementedByDOI:10.5517/cc11vqm7en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624301en
dc.relation.isSupplementedByJia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 981179: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11xzywen
dc.relation.isSupplementedByDOI:10.5517/cc11xzywen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624303en
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