Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

Valerie H. L. Wong; Sai V. C. Vummaleti; Luigi Cavallo; Andrew J. P. White; Steven P. Nolan; King Kuok Mimi Hii

doi:10.1002/chem.201601762

Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

Valerie H. L. Wong, Sai V. C. Vummaleti, Luigi Cavallo, Andrew J. P. White, Steven P. Nolan, King Kuok Mimi Hii

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

13 Scopus citations

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

Original language	English (US)
Pages (from-to)	13320-13327
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	37
DOIs	https://doi.org/10.1002/chem.201601762
State	Published - Aug 2 2016

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10.1002/chem.201601762

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CCDC 1449335: Experimental Crystal Structure Determination : (1,3-bis(2,6-di-isopropylphenyl)imidazolidin-2-ylidene)-(4-methylbenzoato)-silver(i) dichloromethane solvate
Wong, V. H. L. (Creator), Vummaleti, S. V. C. (Creator), Cavallo, L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator), Hii, K. K. M. (Creator), Wong, V. H. L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator) & Hii, K. K. M. (Creator), Cambridge Crystallographic Data Centre, Dec 14 2016
DOI: 10.5517/ccdc.csd.cc1kn4r3, http://hdl.handle.net/10754/624565
Dataset
CCDC 1449333: Experimental Crystal Structure Determination : Acetato-(1,3-bis(2,6-di-isopropylphenyl)imidazolidin-2-ylidene)-silver(i) dichloromethane solvate
Wong, V. H. L. (Creator), Vummaleti, S. V. C. (Creator), Cavallo, L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator), Hii, K. K. M. (Creator), Wong, V. H. L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator) & Hii, K. K. M. (Creator), Cambridge Crystallographic Data Centre, Dec 14 2016
DOI: 10.5517/ccdc.csd.cc1kn4p1, http://hdl.handle.net/10754/624563
Dataset
CCDC 1449338: Experimental Crystal Structure Determination : Benzoato-(1,3-bis(tricyclo[3.3.1.13,7]decan-1-yl)-2,3-dihydro-1H-imidazol-2-ylidene)-silver(i)
Wong, V. H. L. (Creator), Vummaleti, S. V. C. (Creator), Cavallo, L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator), Hii, K. K. M. (Creator), Wong, V. H. L. (Creator), White, A. J. P. (Creator), Nolan, S. P. (Creator) & Hii, K. K. M. (Creator), Cambridge Crystallographic Data Centre, Dec 14 2016
DOI: 10.5517/ccdc.csd.cc1kn4v6, http://hdl.handle.net/10754/624568
Dataset

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@article{72e3223f610141b2ab1ebcf06e1d330a,

title = "Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes",

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. {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

author = "Wong, {Valerie H. L.} and Vummaleti, {Sai V. C.} and Luigi Cavallo and White, {Andrew J. P.} and Nolan, {Steven P.} and Hii, {King Kuok Mimi}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

year = "2016",

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doi = "10.1002/chem.201601762",

language = "English (US)",

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journal = "Chemistry - A European Journal",

issn = "0947-6539",

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T1 - Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

AU - Wong, Valerie H. L.

AU - Vummaleti, Sai V. C.

AU - Cavallo, Luigi

AU - White, Andrew J. P.

AU - Nolan, Steven P.

AU - Hii, King Kuok Mimi

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2016/8/2

Y1 - 2016/8/2

N2 - 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

AB - 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

UR - http://hdl.handle.net/10754/621714

UR - http://doi.wiley.com/10.1002/chem.201601762

UR - http://www.scopus.com/inward/record.url?scp=84984963150&partnerID=8YFLogxK

U2 - 10.1002/chem.201601762

DO - 10.1002/chem.201601762

M3 - Article

C2 - 27483036

VL - 22

SP - 13320

EP - 13327

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 37

ER -

Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

Abstract

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CCDC 1449335: Experimental Crystal Structure Determination : (1,3-bis(2,6-di-isopropylphenyl)imidazolidin-2-ylidene)-(4-methylbenzoato)-silver(i) dichloromethane solvate

CCDC 1449333: Experimental Crystal Structure Determination : Acetato-(1,3-bis(2,6-di-isopropylphenyl)imidazolidin-2-ylidene)-silver(i) dichloromethane solvate

CCDC 1449338: Experimental Crystal Structure Determination : Benzoato-(1,3-bis(tricyclo[3.3.1.13,7]decan-1-yl)-2,3-dihydro-1H-imidazol-2-ylidene)-silver(i)

Cite this