Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

Handle URI:
http://hdl.handle.net/10754/621714
Title:
Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes
Authors:
Wong, Valerie H. L.; Vummaleti, Sai V. C. ( 0000-0001-7276-2475 ) ; Cavallo, Luigi ( 0000-0002-1398-338X ) ; White, Andrew J. P.; Nolan, Steven P.; Hii, King Kuok Mimi ( 0000-0002-1163-0505 )
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
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
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.
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
3-Aug-2016
DOI:
10.1002/chem.201601762
Type:
Article
ISSN:
0947-6539
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.
Is Supplemented By:
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:http://hdl.handle.net/10754/624559; 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:http://hdl.handle.net/10754/624560; 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:http://hdl.handle.net/10754/624561; 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:http://hdl.handle.net/10754/624562; 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:http://hdl.handle.net/10754/624567; 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:http://hdl.handle.net/10754/624568; 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:http://hdl.handle.net/10754/624569; 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:http://hdl.handle.net/10754/624570; 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:http://hdl.handle.net/10754/624571; 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:http://hdl.handle.net/10754/624572; 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:http://hdl.handle.net/10754/624573; 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:http://hdl.handle.net/10754/624563; 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:http://hdl.handle.net/10754/624564; 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:http://hdl.handle.net/10754/624565; 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:http://hdl.handle.net/10754/624566
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorWong, Valerie H. L.en
dc.contributor.authorVummaleti, Sai V. C.en
dc.contributor.authorCavallo, Luigien
dc.contributor.authorWhite, Andrew J. P.en
dc.contributor.authorNolan, Steven P.en
dc.contributor.authorHii, King Kuok Mimien
dc.date.accessioned2016-11-03T13:23:22Z-
dc.date.available2016-11-03T13:23:22Z-
dc.date.issued2016-08-03en
dc.identifier.citationWong 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.en
dc.identifier.issn0947-6539en
dc.identifier.doi10.1002/chem.201601762en
dc.identifier.urihttp://hdl.handle.net/10754/621714-
dc.description.abstractA 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, Weinheimen
dc.description.sponsorshipThe 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.en
dc.publisherWiley-Blackwellen
dc.subjectcarboxylate ligandsen
dc.subjectcatalysisen
dc.subjectligand effectsen
dc.subjectN-heterocyclic carbeneen
dc.subjectsilveren
dc.titleSynthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionDepartment of Chemistry; Imperial College London; Exhibition Road, South Kensington London SW7 2AZ UKen
dc.contributor.institutionDepartment of Chemistry; National University of Singapore; 3 Science Drive Kent Ridge Crescent Singaporeen
dc.contributor.institutionChemistry Department, College of Science; King Saud University; Riyadh 11451 Saudi Arabiaen
dc.contributor.institutionDepartment of Inorganic and Physical Chemistry; Universiteit Gent; Krijgslaan 281 - S3 9000 Ghent Belgiumen
kaust.authorVummaleti, Sai V. C.en
kaust.authorCavallo, Luigien
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