Insertion reactions and structural studies of [(NHC)CuH]2 with nitrogen-based substrates

Tran, Ba L.; Erickson, Jeremy D.

doi:10.1016/j.poly.2023.116811

Insertion reactions and structural studies of [(NHC)CuH]₂ with nitrogen-based substrates

Journal Article · Wed Dec 20 00:00:00 EST 2023 · Polyhedron

DOI:https://doi.org/10.1016/j.poly.2023.116811· OSTI ID:2337425

^[1]; Erickson, Jeremy D. ^[1]

Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Institute for Integrated Catalysis

The stoichiometric and catalytic reactions of Cu-H dimers supported by N-heterocyclic carbenes (NHCs) have mainly focused on the insertions of aldehydes, ketones, CO₂, and unsaturated hydrocarbons. Here we investigated the stoichiometric reactions of dimeric [(NHC)CuH]₂ (NHC = IPr*, 6Dipp) with unsaturated nitrogen-based substrates of PhN=NPh, N₃Ad, pyrazine, and N₂O. The spectroscopic and structural chacterizations of the resulting monomeric, two-coordinate Cu(I) complexes containing diphenyl hydrazido, triazenido, pyrazinyl, and hydroxide ligands are discussed. The hydrazido complex of (IPr*)Cu(NPh-NHPh) and triazenido complex of (IPr*)Cu(HNNNAd) are resistant to N—N bond cleavage and loss of N₂, respectively, to form the corresponding amido complexes even when heated at 80 °C over several hours.

View Accepted Manuscript (DOE)

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 2337425

Report Number(s):: PNNL-SA--193574

Journal Information:: Polyhedron, Journal Name: Polyhedron Vol. 249; ISSN 0277-5387

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Hydrogenation of Carbon Dioxide to Formate Catalyzed by a Copper/1,8-Diazabicyclo[5.4.0]undec-7-ene System Watari, Ryo; Kayaki, Yoshihito; Hirano, Shin-ichi Advanced Synthesis & Catalysis, Vol. 357, Issue 7 https://doi.org/10.1002/adsc.201500043	journal	April 2015
Polishing a Diamond in the Rough: “CuH” Catalysis with Silanes Rendler, Sebastian; Oestreich, Martin Angewandte Chemie International Edition, Vol. 46, Issue 4 https://doi.org/10.1002/anie.200602668	journal	January 2007
Regio‐ and Enantioselective Copper(I)‐Catalyzed Hydroboration of Borylalkenes: Asymmetric Synthesis of 1,1‐Diborylalkanes Feng, Xinhui; Jeon, Heekyung; Yun, Jaesook Angewandte Chemie International Edition, Vol. 52, Issue 14 https://doi.org/10.1002/anie.201208610	journal	February 2013
Bonding and Reactivity of a μ-Hydrido Dicopper Cation Wyss, Chelsea M.; Tate, Brandon K.; Bacsa, John Angewandte Chemie International Edition, Vol. 52, Issue 49 https://doi.org/10.1002/anie.201306736	journal	October 2013
Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes Pirnot, Michael T.; Wang, Yi-Ming; Buchwald, Stephen L. Angewandte Chemie International Edition, Vol. 55, Issue 1 https://doi.org/10.1002/anie.201507594	journal	December 2015
Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo Angewandte Chemie International Edition, Vol. 55, Issue 5 https://doi.org/10.1002/anie.201509288	journal	December 2015
Single‐Crystal to Single‐Crystal Transformations: Stepwise CO₂ Insertions into Bridging Hydrides of [(NHC)CuH]₂ Complexes Patrick, Evan A.; Bowden, Mark E.; Erickson, Jeremy D. Angewandte Chemie International Edition, Vol. 62, Issue 30 https://doi.org/10.1002/anie.202304648	journal	June 2023
CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition Liu, Richard Y.; Buchwald, Stephen L. Accounts of Chemical Research, Vol. 53, Issue 6 https://doi.org/10.1021/acs.accounts.0c00164	journal	May 2020
Coinage Metal Hydrides: Synthesis, Characterization, and Reactivity Jordan, Abraham J.; Lalic, Gojko; Sadighi, Joseph P. Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00366	journal	June 2016
Catalytic Nitrous Oxide Reduction with H₂ Mediated by Pincer Ir Complexes Ortega-Lepe, Isabel; Sánchez, Práxedes; Santos, Laura L. Inorganic Chemistry, Vol. 61, Issue 46 https://doi.org/10.1021/acs.inorgchem.2c02963	journal	November 2022
Synthesis and Reactivity of New Copper(I) Hydride Dimers Jordan, Abraham J.; Wyss, Chelsea M.; Bacsa, John Organometallics, Vol. 35, Issue 5 https://doi.org/10.1021/acs.organomet.6b00025	journal	February 2016
Copper, Silver, and Gold Complexes in Hydrosilylation Reactions Díez-González, Silvia; Nolan, Steven P. Accounts of Chemical Research, Vol. 41, Issue 2 https://doi.org/10.1021/ar7001655	journal	February 2008
CuH-Catalyzed Reactions Deutsch, Carl; Krause, Norbert; Lipshutz, Bruce H. Chemical Reviews, Vol. 108, Issue 8 https://doi.org/10.1021/cr0684321	journal	August 2008
Asymmetric Hydrogenation of Heteroarenes and Arenes Wang, Duo-Sheng; Chen, Qing-An; Lu, Sheng-Mei Chemical Reviews, Vol. 112, Issue 4, p. 2557-2590 https://doi.org/10.1021/cr200328h	journal	November 2011
Synthesis and molecular geometry of hexameric triphenylphosphinocopper(I) hydride and the crystal structure of H6Cu6(PPh3)6. HCONMe2 [hexameric triphenylphosphino copper(I) hydride dimethylformamide] Churchill, Melvyn Rowen.; Bezman, Susan A.; Osborn, John A. Inorganic Chemistry, Vol. 11, Issue 8 https://doi.org/10.1021/ic50114a015	journal	August 1972
Hydride-mediated homogeneous catalysis. Catalytic reduction of .alpha.,.beta.-unsaturated ketones using [(Ph3P)CuH]6 and H2 Mahoney, Wayne S.; Stryker, Jeffrey M. Journal of the American Chemical Society, Vol. 111, Issue 24 https://doi.org/10.1021/ja00206a008	journal	November 1989
Selective hydride-mediated conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds using [(Ph3P)CuH]6 Mahoney, Wayne S.; Brestensky, Donna M.; Stryker, Jeffrey M. Journal of the American Chemical Society, Vol. 110, Issue 1 https://doi.org/10.1021/ja00209a048	journal	January 1988
Selective O-atom transfer from nitrous oxide to hydride and aryl ligands of bis(pentamethylcyclopentadienyl)hafnium derivatives Vaughan, G. Alan; Rupert, Peter B.; Hillhouse, Gregory L. Journal of the American Chemical Society, Vol. 109, Issue 18 https://doi.org/10.1021/ja00252a047	journal	September 1987
Soluble copper hydrides: solution behavior and reactions related to carbon monoxide hydrogenation Goeden, Gary V.; Caulton, Kenneth G. Journal of the American Chemical Society, Vol. 103, Issue 24 https://doi.org/10.1021/ja00414a062	journal	December 1981
Nature of soluble copper(I) hydride Dilts, J. A.; Shriver, D. F. Journal of the American Chemical Society, Vol. 90, Issue 21 https://doi.org/10.1021/ja01023a020	journal	October 1968
Reaction of copper(I) hydride with organocopper(I) compounds Whitesides, George M.; San Filippo, Joseph; Stredronsky, Erwin R. Journal of the American Chemical Society, Vol. 91, Issue 23 https://doi.org/10.1021/ja01051a093	journal	November 1969
NN Bond Cleavage by a Low-Coordinate Iron(II) Hydride Complex Smith, Jeremy M.; Lachicotte, Rene J.; Holland, Patrick L. Journal of the American Chemical Society, Vol. 125, Issue 51 https://doi.org/10.1021/ja038152s	journal	December 2003
Mechanistic Insight into NN Cleavage by a Low-Coordinate Iron(II) Hydride Complex Sadique, Azwana R.; Gregory, Elizabeth A.; Brennessel, William W. Journal of the American Chemical Society, Vol. 129, Issue 26 https://doi.org/10.1021/ja069199r	journal	July 2007
Facile Hydrogenation of N₂O by an Operationally Unsaturated Osmium Polyhydride Lee, Joo-Ho; Pink, Maren; Tomaszewski, John Journal of the American Chemical Society, Vol. 129, Issue 28 https://doi.org/10.1021/ja071452f	journal	June 2007
Catalytic Anti-Markovnikov Hydrobromination of Alkynes Uehling, Mycah R.; Rucker, Richard P.; Lalic, Gojko Journal of the American Chemical Society, Vol. 136, Issue 24 https://doi.org/10.1021/ja503944n	journal	June 2014
The Reactivity Patterns of Low-Coordinate Iron−Hydride Complexes Yu, Ying; Sadique, Azwana R.; Smith, Jeremy M. Journal of the American Chemical Society, Vol. 130, Issue 20 https://doi.org/10.1021/ja710669w	journal	May 2008
Synthesis, Structural Characterization, and CO₂Reactivity of a Constitutionally Analogous Series of Tricopper Mono-, Di-, and Trihydrides Beamer, Andrew W.; Buss, Joshua A. Journal of the American Chemical Society, Vol. 145, Issue 23 https://doi.org/10.1021/jacs.3c04170	journal	June 2023
Mechanism of Copper-Catalyzed Hydroalkylation of Alkynes: An Unexpected Role of Dinuclear Copper Complexes Suess, Alison M.; Uehling, Mycah R.; Kaminsky, Werner Journal of the American Chemical Society, Vol. 137, Issue 24 https://doi.org/10.1021/jacs.5b03086	journal	June 2015
Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration Xi, Yumeng; Hartwig, John F. Journal of the American Chemical Society, Vol. 138, Issue 21 https://doi.org/10.1021/jacs.6b02478	journal	May 2016
Triphosphine-Ligated Copper Hydrides for CO ₂ Hydrogenation: Structure, Reactivity, and Thermodynamic Studies Zall, Christopher M.; Linehan, John C.; Appel, Aaron M. Journal of the American Chemical Society, Vol. 138, Issue 31 https://doi.org/10.1021/jacs.6b05349	journal	August 2016
Catalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes Mailig, Melrose; Hazra, Avijit; Armstrong, Megan K. Journal of the American Chemical Society, Vol. 139, Issue 20 https://doi.org/10.1021/jacs.7b02104	journal	May 2017
Hydrogenation and Hydrosilylation of Nitrous Oxide Homogeneously Catalyzed by a Metal Complex Zeng, Rong; Feller, Moran; Ben-David, Yehoshoa Journal of the American Chemical Society, Vol. 139, Issue 16 https://doi.org/10.1021/jacs.7b02124	journal	April 2017
Mechanistic Studies of Copper-Catalyzed Asymmetric Hydroboration of Alkenes Xi, Yumeng; Hartwig, John F. Journal of the American Chemical Society, Vol. 139, Issue 36 https://doi.org/10.1021/jacs.7b07124	journal	September 2017
Monosubstituted triazenido complexes as intermediates in the formation of amido complexes from hafnium hydrides and aryl azides Hillhouse, Gregory L.; Bercaw, John E. Organometallics, Vol. 1, Issue 8 https://doi.org/10.1021/om00068a003	journal	August 1982
Synthesis, Structure, and Alkyne Reactivity of a Dimeric (Carbene)copper(I) Hydride Mankad, Neal P.; Laitar, David S.; Sadighi, Joseph P. Organometallics, Vol. 23, Issue 14, p. 3369-3371 https://doi.org/10.1021/om0496380	journal	July 2004
Copper-Catalyzed Hydroboration of Carbon Dioxide Shintani, Ryo; Nozaki, Kyoko Organometallics, Vol. 32, Issue 8 https://doi.org/10.1021/om400175h	journal	April 2013
Nitrous Oxide Mediated Synthesis of Monomeric Hydroxoruthenium Complexes. Reactivity of (DMPE) ₂ Ru(H)(OH) and the Synthesis of a Silica-Bound Ruthenium Complex Kaplan, Anne W.; Bergman, Robert G. Organometallics, Vol. 17, Issue 23 https://doi.org/10.1021/om980295d	journal	October 1998
Tandem copper hydride–Lewis pair catalysed reduction of carbon dioxide into formate with dihydrogen Romero, Erik A.; Zhao, Tianxiang; Nakano, Ryo Nature Catalysis, Vol. 1, Issue 10 https://doi.org/10.1038/s41929-018-0140-3	journal	October 2018
Synthetic chemistry with nitrous oxide Severin, Kay Chemical Society Reviews, Vol. 44, Issue 17 https://doi.org/10.1039/C5CS00339C	journal	January 2015
N-heterocyclic carbene copper( i ) catalysed N-methylation of amines using CO 2 Santoro, Orlando; Lazreg, Faïma; Minenkov, Yury Dalton Transactions, Vol. 44, Issue 41 https://doi.org/10.1039/C5DT03506F	journal	January 2015
N-Insertion reaction mechanisms of phenyl azides with a hafnium hydride complex: a quantum chemistry calculation Xie, Hujun; Wang, Lihong; Li, Yang New Journal of Chemistry, Vol. 41, Issue 12 https://doi.org/10.1039/C7NJ00411G	journal	January 2017
Hydrogenation reactions catalyzed by HN(CH ₂ CH ₂ PR ₂ ) ₂ -ligated copper complexes Ekanayake, Dewmi A.; Chakraborty, Arundhoti; Krause, Jeanette A. Inorganic Chemistry Frontiers, Vol. 8, Issue 21 https://doi.org/10.1039/D1QI00776A	journal	January 2021
Accelerating the insertion reactions of (NHC)Cu–H via remote ligand functionalization Speelman, Amy L.; Tran, Ba L.; Erickson, Jeremy D. Chemical Science, Vol. 12, Issue 34 https://doi.org/10.1039/D1SC01911B	journal	January 2021
N-Heterocyclic carbene (NHC)–copper-catalysed transformations of carbon dioxide Zhang, Liang; Hou, Zhaomin Chemical Science, Vol. 4, Issue 9 https://doi.org/10.1039/c3sc51070k	journal	January 2013
Regioselective transformation of alkynes catalyzed by a copper hydride or boryl copper species Fujihara, Tetsuaki; Semba, Kazuhiko; Terao, Jun Catalysis Science & Technology, Vol. 4, Issue 6 https://doi.org/10.1039/c4cy00070f	journal	January 2014
OLEX2 : a complete structure solution, refinement and analysis program Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J. Journal of Applied Crystallography, Vol. 42, Issue 2 https://doi.org/10.1107/S0021889808042726	journal	January 2009

Similar Records

Single‐Crystal to Single‐Crystal Transformations: Stepwise CO ₂ Insertions into Bridging Hydrides of [(NHC)CuH] ₂ Complexes

Journal Article · Wed Jun 14 20:00:00 EDT 2023 · Angewandte Chemie · OSTI ID:1985197

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Azide
N-heterocyclic carbene
Pyrazine
copper hydride
insertion
nitrous oxide

CCDC 2297413: Experimental Crystal Structure Determination L., Tran, Ba; D., Erickson, Jeremy https://doi.org/10.5517/ccdc.csd.cc2h3n3d The current record is supplemented by this dataset	dataset	January 2024
CCDC 2297414: Experimental Crystal Structure Determination L., Tran, Ba; D., Erickson, Jeremy https://doi.org/10.5517/ccdc.csd.cc2h3n4f The current record is supplemented by this dataset	dataset	January 2024
CCDC 2297415: Experimental Crystal Structure Determination L., Tran, Ba; D., Erickson, Jeremy https://doi.org/10.5517/ccdc.csd.cc2h3n5g The current record is supplemented by this dataset	dataset	January 2024

Insertion reactions and structural studies of [(NHC)CuH]2 with nitrogen-based substrates

Citation Formats

References (46)

Linked Research (3)

Similar Records

Related Subjects

Insertion reactions and structural studies of [(NHC)CuH]₂ with nitrogen-based substrates