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Reduction of a Chelating Bis(NHC) Palladium(II) Complex to [{μ‐bis(NHC)} 2 Pd 2 H] + : A Terminal Hydride in a Binuclear Palladium(I) Species Formed under Catalytically Relevant Conditions

2010; Wiley; Volume: 49; Issue: 36 Linguagem: Inglês

10.1002/anie.201003177

ISSN

1521-3773

Autores

Peter Boyd, Alison J. Edwards, Michael G. Gardiner, Curtis C. Ho, M. H. Lemée-Cailleau, David S. McGuinness, Anung Riapanitra, Jonathan W. Steed, Damien N. Stringer, Brian F. Yates,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

Angewandte Chemie International EditionVolume 49, Issue 36 p. 6315-6318 Communication Reduction of a Chelating Bis(NHC) Palladium(II) Complex to [{μ-bis(NHC)}2Pd2H]+: A Terminal Hydride in a Binuclear Palladium(I) Species Formed under Catalytically Relevant Conditions† Peter D. W. Boyd Prof., Peter D. W. Boyd Prof. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858 Current address: Department of Chemistry, The University of Auckland, Auckland 1142 (New Zealand)Search for more papers by this authorAlison J. Edwards Dr., Alison J. Edwards Dr. Bragg Institute, Australian Nuclear Science and Technology Organisation, PMB 1, Menai NSW 2234 (Australia)Search for more papers by this authorMichael G. Gardiner Dr., Michael G. Gardiner Dr. [email protected] School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorCurtis C. Ho, Curtis C. Ho School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorMarie-Hélène Lemée-Cailleau Dr., Marie-Hélène Lemée-Cailleau Dr. Institut Laue-Langevin, B.P.156, 6 rue Jules Horowitz, 38042 Grenoble Cedex 9 (France)Search for more papers by this authorDavid S. McGuinness Dr., David S. McGuinness Dr. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorAnung Riapanitra, Anung Riapanitra School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858 Current address: Department of Chemistry, Universitas Jenderal Soedirman, Jl. Dr. Soeparno 61, Purwokerto 53123 (Indonesia)Search for more papers by this authorJonathan W. Steed Prof., Jonathan W. Steed Prof. Department of Chemistry, South Road, University of Durham, Durham DH1 3LE (UK)Search for more papers by this authorDamien N. Stringer Dr., Damien N. Stringer Dr. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorBrian F. Yates Prof., Brian F. Yates Prof. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this author Peter D. W. Boyd Prof., Peter D. W. Boyd Prof. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858 Current address: Department of Chemistry, The University of Auckland, Auckland 1142 (New Zealand)Search for more papers by this authorAlison J. Edwards Dr., Alison J. Edwards Dr. Bragg Institute, Australian Nuclear Science and Technology Organisation, PMB 1, Menai NSW 2234 (Australia)Search for more papers by this authorMichael G. Gardiner Dr., Michael G. Gardiner Dr. [email protected] School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorCurtis C. Ho, Curtis C. Ho School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorMarie-Hélène Lemée-Cailleau Dr., Marie-Hélène Lemée-Cailleau Dr. Institut Laue-Langevin, B.P.156, 6 rue Jules Horowitz, 38042 Grenoble Cedex 9 (France)Search for more papers by this authorDavid S. McGuinness Dr., David S. McGuinness Dr. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorAnung Riapanitra, Anung Riapanitra School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858 Current address: Department of Chemistry, Universitas Jenderal Soedirman, Jl. Dr. Soeparno 61, Purwokerto 53123 (Indonesia)Search for more papers by this authorJonathan W. Steed Prof., Jonathan W. Steed Prof. Department of Chemistry, South Road, University of Durham, Durham DH1 3LE (UK)Search for more papers by this authorDamien N. Stringer Dr., Damien N. Stringer Dr. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this authorBrian F. Yates Prof., Brian F. Yates Prof. School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS 7001 (Australia), Fax: (+61) 3-6229-2858Search for more papers by this author First published: 19 August 2010 https://doi.org/10.1002/anie.201003177Citations: 41 † X-ray data were obtained on MX1 at the Australian Synchrotron, Victoria, Australia. 29 We thank the Australian Government for an Australian Partnership Scholarship (APS) under the Australia Indonesia Partnership for Reconstruction and Development (AIPRD), The University of Auckland for research and study leave support, and Dr. Ross O. Piltz for assistance with neutron data reduction. NHC=N-heterocyclic carbene ligand. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Half-way house: The first palladium(I) N-heterocyclic carbene complex has been isolated in high yield by the base-assisted reduction of a palladium(II) precursor. The location of the unique terminal hydride (see picture; PdI cyan, H white, N blue) was established by neutron crystal structure determination, and the solution fluxional behavior of the complex was explored. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201003177_sm_miscellaneous_information.pdf1.1 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aW. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602–2605; 10.1002/ange.19951072124 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 2371–2374; 10.1002/anie.199523711 CASWeb of Science®Google Scholar 1bS. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612–3676. 10.1021/cr900074m CASPubMedWeb of Science®Google Scholar 2 2aE. A. B. Kantchev, C. J. 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X-ray and neutron data for prismatic crystals from MeOH are given in the caption of Figure 1. Details of all forms are given below and the Supporting Information. X-ray and neutron crystal data for 2: Needles from MeOH (X-ray), C50H57F6N8PPd2 (Mr=1127.81): recorded at 100 K with synchrotron radiation (0.75277 Å), crystal dimensions 0.10 mm×0.03 mm×0.03 mm, μ=0.786 mm−1, tetragonal, space group P4/ncc, a=28.514(5), c=25.560(5) Å, V=20 782(6) Å3, Z=16, R=0.045 for 6850 (I>2 σ(I)) data and wR=0.119 for 8258 all data (2 θmax=48.26°, Rint=0.103). Prisms from MeOH (X-ray), C50H57F6N8PPd2 (Mr=1127.81): recorded at 100 K with synchrotron radiation (0.75277 Å), crystal dimensions 0.25 mm×0.15 mm×0.15 mm, μ=0.814 mm−1, monoclinic, space group P21/c, a=13.244(2), b=18.185(2), c=21.6080(14) Å, β=105.487(4)°, V=5015.2(11) Å3, Z=4, R=0.041 for 7456 (I>2 σ(I)) data and wR=0.099 for 7565 all data (2 θmax=51.26°, Rint=0.092). Prisms from THF (X-ray), C50H57F6N8PPd2⋅4 (C4H8O) (Mr=1416.22): recorded at 193 K with MoKα radiation (0.71073 Å), crystal dimensions 0.5 mm×0.4 mm×0.4 mm, μ=0.604 mm−1, orthorhombic, space group Aba2, a=20.370(9), b=14.510(4), c=23.631(5) Å, V=6984(4) Å3, Z=4, R=0.136 for 3924 (I>2 σ(I)) data and wR=0.115 for 4346 all data (2 θmax=50.24°, Rint=0.035). Prisms from MeOH (neutron): recorded at 100 K with white-beam radiation (0.8–5.4 Å), crystal dimensions 0.7 mm×0.3 mm×0.3 mm, monoclinic, space group P21/c, a=13.240(3), b=18.190(4), c=21.610(4) Å, β=105.49(3)°, V=5015.5(19) Å3, Z=4, R=0.041 for 2837 (I>2 σ(I)) data and wR=0.099 for 3882 all data (2 θmax=42.58°, Rint=0.212). Prisms from THF (neutron): recorded at 150 K with white-beam radiation (1.0–1.8 Å), crystal dimensions 1.8 mm×1.2 mm×1.0 mm, orthorhombic, space group Aba2, a=20.370(4), b=14.510(3), c=23.630(5) Å, V=6985(2) Å3, Z=4, R=0.122 for 1102 (I>3 σ(I)) data and wR=0.125 for 1413 all data (2 θmax=41.74°, Rint=0.130). 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