The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid

Julie Broggi; Václav Jurčík; Olivier Songis; Albert Poater; Luigi Cavallo; Alexandra M. Z. Slawin; Catherine S. J. Cazin

doi:10.1021/ja311087c

The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid

Julie Broggi, Václav Jurčík, Olivier Songis, Albert Poater, Luigi Cavallo, Alexandra M. Z. Slawin, Catherine S. J. Cazin

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

95 Scopus citations

Abstract

The [Pd(SIPr)(PCy3)] complex efficiently promotes a tandem process involving dehydrogenation of formic acid and hydrogenation of C-C multiple bonds using H2 formed in situ. The isolation of a key catalytic hydridoformatopalladium species, [Pd{OC(O)H}(H)(IPr)(PCy 3)], is reported. The complex plays a key role in the Pd(0)-mediated formation of hydrogen from formic acid. Mechanistic and computational studies delineate the operational role of the palladium complex in this efficient tandem sequence. © 2013 American Chemical Society.

Original language	English (US)
Pages (from-to)	4588-4591
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	12
DOIs	https://doi.org/10.1021/ja311087c
State	Published - Jan 14 2013

ASJC Scopus subject areas

Biochemistry
Colloid and Surface Chemistry
General Chemistry
Catalysis

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10.1021/ja311087c

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@article{4d65c8b36fb34d188897b5ecb10ed594,

title = "The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid",

abstract = "The [Pd(SIPr)(PCy3)] complex efficiently promotes a tandem process involving dehydrogenation of formic acid and hydrogenation of C-C multiple bonds using H2 formed in situ. The isolation of a key catalytic hydridoformatopalladium species, [Pd{OC(O)H}(H)(IPr)(PCy 3)], is reported. The complex plays a key role in the Pd(0)-mediated formation of hydrogen from formic acid. Mechanistic and computational studies delineate the operational role of the palladium complex in this efficient tandem sequence. {\textcopyright} 2013 American Chemical Society.",

author = "Julie Broggi and V{\'a}clav Jur{\v c}{\'i}k and Olivier Songis and Albert Poater and Luigi Cavallo and Slawin, {Alexandra M. Z.} and Cazin, {Catherine S. J.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The EPSRC and the Royal Society (University Research Fellowship to C.S.J.C.), the Spanish MICINN (Ramon y Cajal Contract RYC-2009-05226 to A.P.), the EC (Career Integration Grant CIG09-GA-2011-293900 to A.P.), and Generalitat de Catalunya (BE Fellowship 2011BE100793 to A.P.) are acknowledged for financial support. Umicore AG is thanked for a generous gift of materials. We thank KAUST graphic artist Ekaterina Mikhaylova for the cover art.",

year = "2013",

month = jan,

day = "14",

doi = "10.1021/ja311087c",

language = "English (US)",

volume = "135",

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journal = "Journal of the American Chemical Society",

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T1 - The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid

AU - Broggi, Julie

AU - Jurčík, Václav

AU - Songis, Olivier

AU - Poater, Albert

AU - Cavallo, Luigi

AU - Slawin, Alexandra M. Z.

AU - Cazin, Catherine S. J.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The EPSRC and the Royal Society (University Research Fellowship to C.S.J.C.), the Spanish MICINN (Ramon y Cajal Contract RYC-2009-05226 to A.P.), the EC (Career Integration Grant CIG09-GA-2011-293900 to A.P.), and Generalitat de Catalunya (BE Fellowship 2011BE100793 to A.P.) are acknowledged for financial support. Umicore AG is thanked for a generous gift of materials. We thank KAUST graphic artist Ekaterina Mikhaylova for the cover art.

PY - 2013/1/14

Y1 - 2013/1/14

N2 - The [Pd(SIPr)(PCy3)] complex efficiently promotes a tandem process involving dehydrogenation of formic acid and hydrogenation of C-C multiple bonds using H2 formed in situ. The isolation of a key catalytic hydridoformatopalladium species, [Pd{OC(O)H}(H)(IPr)(PCy 3)], is reported. The complex plays a key role in the Pd(0)-mediated formation of hydrogen from formic acid. Mechanistic and computational studies delineate the operational role of the palladium complex in this efficient tandem sequence. © 2013 American Chemical Society.

AB - The [Pd(SIPr)(PCy3)] complex efficiently promotes a tandem process involving dehydrogenation of formic acid and hydrogenation of C-C multiple bonds using H2 formed in situ. The isolation of a key catalytic hydridoformatopalladium species, [Pd{OC(O)H}(H)(IPr)(PCy 3)], is reported. The complex plays a key role in the Pd(0)-mediated formation of hydrogen from formic acid. Mechanistic and computational studies delineate the operational role of the palladium complex in this efficient tandem sequence. © 2013 American Chemical Society.

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DO - 10.1021/ja311087c

M3 - Article

SN - 0002-7863

VL - 135

SP - 4588

EP - 4591

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 12

ER -

The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid

Abstract

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CCDC 873769: Experimental Crystal Structure Determination : (1,3-bis(2,6-Di-isopropylphenyl)imidazol-2-ylidene)-(formato-O)-hydrido-(tricyclohexylphosphine)-palladium tetrahydrofuran solvate

Cite this

The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 873769: Experimental Crystal Structure Determination : (1,3-bis(2,6-Di-isopropylphenyl)imidazol-2-ylidene)-(formato-O)-hydrido-(tricyclohexylphosphine)-palladium tetrahydrofuran solvate

Cite this