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

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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

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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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.",

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month = aug,

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doi = "10.1002/chem.201601762",

language = "English (US)",

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journal = "Chemistry - A European Journal",

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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

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DO - 10.1002/chem.201601762

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C2 - 27483036

SN - 0947-6539

VL - 22

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EP - 13327

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 37

ER -

Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

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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 1449341: Experimental Crystal Structure Determination : (1,3-bis(2,6-bis(pentan-3-yl)phenyl)-2,3-dihydro-1H-imidazol-2-ylidene)-(4-chlorobenzoato)-silver(i)

CCDC 1449339: Experimental Crystal Structure Determination : Acetato-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)-2,3-dihydro-1H-imidazol-2-ylidene)-silver(i) n-hexane solvate

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Synthesis, Structure and Catalytic Activity of NHC-AgICarboxylate Complexes

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Datasets

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

CCDC 1449341: Experimental Crystal Structure Determination : (1,3-bis(2,6-bis(pentan-3-yl)phenyl)-2,3-dihydro-1H-imidazol-2-ylidene)-(4-chlorobenzoato)-silver(i)

CCDC 1449339: Experimental Crystal Structure Determination : Acetato-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)-2,3-dihydro-1H-imidazol-2-ylidene)-silver(i) n-hexane solvate

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