Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

Type
Article
Authors
Wong, Valerie H. L.
Vummaleti, Sai V. C. cc
Cavallo, Luigi cc
White, Andrew J. P.
Nolan, Steven P. cc
Hii, King Kuok Mimi cc
KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2016-08-02
Online Publication Date
2016-08-02
Print Publication Date
2016-09-05
Permanent link to this record
http://hdl.handle.net/10754/621714

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Abstract
A general synthetic route was used to prepare 15 new N-heterocyclic carbene (NHC)–AgI complexes bearing anionic carboxylate ligands [Ag(NHC)(O2CR)], including a homologous series of complexes of sterically flexible ITent ligands, which permit a systematic spectroscopic and theoretical study of the structural and electronic features of these compounds. The complexes displayed a significant ligand-accelerated effect in the intramolecular cyclisation of propargylic amides to oxazolidines. The substrate scope is highly complementary to that previously achieved by NHC–Au and pyridyl–AgI complexes. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Citation
Wong VHL, Vummaleti SVC, Cavallo L, White AJP, Nolan SP, et al. (2016) Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes. Chemistry - A European Journal 22: 13320–13327. Available: http://dx.doi.org/10.1002/chem.201601762.
Sponsors
The authors are grateful to NUS and the Imperial College London for the award of a scholarship (to V.H.L.W.). L.C. and S.P.N. thank the KAUST for support through the CCF project.
Publisher
Wiley
Journal
Chemistry - A European Journal
DOI
10.1002/chem.201601762
PubMed ID
27483036
Relations
Is Supplemented By:
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449329: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4kx. DOI: 10.5517/ccdc.csd.cc1kn4kx HANDLE: 10754/624559
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449330: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4ly. DOI: 10.5517/ccdc.csd.cc1kn4ly HANDLE: 10754/624560
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449331: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4mz. DOI: 10.5517/ccdc.csd.cc1kn4mz HANDLE: 10754/624561
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449332: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4n0. DOI: 10.5517/ccdc.csd.cc1kn4n0 HANDLE: 10754/624562
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449337: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4t5. DOI: 10.5517/ccdc.csd.cc1kn4t5 HANDLE: 10754/624567
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449338: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4v6. DOI: 10.5517/ccdc.csd.cc1kn4v6 HANDLE: 10754/624568
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449339: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4w7. DOI: 10.5517/ccdc.csd.cc1kn4w7 HANDLE: 10754/624569
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449340: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4x8. DOI: 10.5517/ccdc.csd.cc1kn4x8 HANDLE: 10754/624570
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449341: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4y9. DOI: 10.5517/ccdc.csd.cc1kn4y9 HANDLE: 10754/624571
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449342: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4zb. DOI: 10.5517/ccdc.csd.cc1kn4zb HANDLE: 10754/624572
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449343: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn50d. DOI: 10.5517/ccdc.csd.cc1kn50d HANDLE: 10754/624573
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449333: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4p1. DOI: 10.5517/ccdc.csd.cc1kn4p1 HANDLE: 10754/624563
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449334: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4q2. DOI: 10.5517/ccdc.csd.cc1kn4q2 HANDLE: 10754/624564
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449335: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4r3. DOI: 10.5517/ccdc.csd.cc1kn4r3 HANDLE: 10754/624565
  • [Dataset]
    Wong, V. H. L., Vummaleti, S. V. C., Cavallo, L., White, A. J. P., Nolan, S. P., & Hii, K. K. (2016). CCDC 1449336: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1kn4s4. DOI: 10.5517/ccdc.csd.cc1kn4s4 HANDLE: 10754/624566
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)