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Title: Spectroscopic Evidence for a Monomeric Copper(I) Hydride and Crystallographic Characterization of a Monomeric Silver(I) Hydride

Authors:
 [1];  [1];  [1];  [1];  [2]; ORCiD logo [1]
  1. Joint UCSD-CNRS Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla CA 92093-0358 USA
  2. UCSD Crystallography Facility, Department of Chemistry and Biochemistry, Urey Hall Room 5128, 9500 Gilman Drive, M/C 0358 La Jolla CA 92093-0358 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1401052
Grant/Contract Number:  
SC0009376
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition) Journal Volume: 56 Journal Issue: 14; Journal ID: ISSN 1433-7851
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Romero, Erik A., Olsen, Pauline M., Jazzar, Rodolphe, Soleilhavoup, Michele, Gembicky, Milan, and Bertrand, Guy. Spectroscopic Evidence for a Monomeric Copper(I) Hydride and Crystallographic Characterization of a Monomeric Silver(I) Hydride. Germany: N. p., 2017. Web. doi:10.1002/anie.201700858.
Romero, Erik A., Olsen, Pauline M., Jazzar, Rodolphe, Soleilhavoup, Michele, Gembicky, Milan, & Bertrand, Guy. Spectroscopic Evidence for a Monomeric Copper(I) Hydride and Crystallographic Characterization of a Monomeric Silver(I) Hydride. Germany. doi:10.1002/anie.201700858.
Romero, Erik A., Olsen, Pauline M., Jazzar, Rodolphe, Soleilhavoup, Michele, Gembicky, Milan, and Bertrand, Guy. Thu . "Spectroscopic Evidence for a Monomeric Copper(I) Hydride and Crystallographic Characterization of a Monomeric Silver(I) Hydride". Germany. doi:10.1002/anie.201700858.
@article{osti_1401052,
title = {Spectroscopic Evidence for a Monomeric Copper(I) Hydride and Crystallographic Characterization of a Monomeric Silver(I) Hydride},
author = {Romero, Erik A. and Olsen, Pauline M. and Jazzar, Rodolphe and Soleilhavoup, Michele and Gembicky, Milan and Bertrand, Guy},
abstractNote = {},
doi = {10.1002/anie.201700858},
journal = {Angewandte Chemie (International Edition)},
number = 14,
volume = 56,
place = {Germany},
year = {2017},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/anie.201700858

Citation Metrics:
Cited by: 9 works
Citation information provided by
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Works referenced in this record:

Carbene-stabilized main group radicals and radical ions
journal, January 2013

  • Martin, Caleb D.; Soleilhavoup, Michele; Bertrand, Guy
  • Chemical Science, Vol. 4, Issue 8
  • DOI: 10.1039/c3sc51174j

Catalyst-free dehydrocoupling of amines, alcohols, and thiols with pinacol borane and 9-borabicyclononane (9-BBN)
journal, January 2016

  • Romero, Erik A.; Peltier, Jesse L.; Jazzar, Rodolphe
  • Chemical Communications, Vol. 52, Issue 69
  • DOI: 10.1039/C6CC06096J

Catalytic Anti-Markovnikov Hydrobromination of Alkynes
journal, June 2014

  • Uehling, Mycah R.; Rucker, Richard P.; Lalic, Gojko
  • Journal of the American Chemical Society, Vol. 136, Issue 24
  • DOI: 10.1021/ja503944n

Ein thermisch stabiles Gold(III)-Hydrid: Synthese, Reaktivität und reduktive Kondensation als Weg zu Gold(II)-Komplexen
journal, September 2012

  • Roşca, Dragoş-Adrian; Smith, Dan A.; Hughes, David L.
  • Angewandte Chemie, Vol. 124, Issue 42
  • DOI: 10.1002/ange.201206468

Feuer und Eis: ein Gold(III)-monohydrid
journal, November 2012


Gold Catalysis
journal, December 2006

  • Hashmi, A. Stephen K.; Hutchings, Graham J.
  • Angewandte Chemie International Edition, Vol. 45, Issue 47
  • DOI: 10.1002/anie.200602454

A Comparison of the Stability and Reactivity of Diamido‐ and Diaminocarbene Copper Alkoxide and Hydride Complexes
journal, August 2015

  • Collins, Lee R.; Riddlestone, Ian M.; Mahon, Mary F.
  • Chemistry – A European Journal, Vol. 21, Issue 40
  • DOI: 10.1002/chem.201502476

Synthesis, Structure, and Alkyne Reactivity of a Dimeric (Carbene)copper(I) Hydride
journal, July 2004

  • Mankad, Neal P.; Laitar, David S.; Sadighi, Joseph P.
  • Organometallics, Vol. 23, Issue 14, p. 3369-3371
  • DOI: 10.1021/om0496380

The Janus Face of the X Ligand in the Copper-Catalyzed Azide–Alkyne Cycloaddition
journal, December 2015

  • Jin, Liqun; Romero, Erik A.; Melaimi, Mohand
  • Journal of the American Chemical Society, Vol. 137, Issue 50
  • DOI: 10.1021/jacs.5b11028

Experimental and Computational Studies of the Copper Borate Complexes [(NHC)Cu(HBEt 3 )] and [(NHC)Cu(HB(C 6 F 5 ) 3 )]
journal, November 2016

  • Collins, Lee R.; Rajabi, Nasir A.; Macgregor, Stuart A.
  • Angewandte Chemie International Edition, Vol. 55, Issue 50
  • DOI: 10.1002/anie.201608081

Cyclic (Alkyl)(Amino)Carbenes (CAACs): Stable Carbenes on the Rise
journal, December 2014

  • Soleilhavoup, Michèle; Bertrand, Guy
  • Accounts of Chemical Research, Vol. 48, Issue 2
  • DOI: 10.1021/ar5003494

Cyclic Alkyl(amino) Carbene Stabilized Complexes with Low Coordinate Metals of Enduring Nature
journal, February 2016

  • Roy, Sudipta; Mondal, Kartik Chandra; Roesky, Herbert W.
  • Accounts of Chemical Research, Vol. 49, Issue 3
  • DOI: 10.1021/acs.accounts.5b00381

Stable Mono- and Dinuclear Organosilver Complexes
journal, December 2016


Intramolecular “Hydroiminiumation” of Alkenes: Application to the Synthesis of Conjugate Acids of Cyclic Alkyl Amino Carbenes (CAACs)
journal, April 2007

  • Jazzar, Rodolphe; Dewhurst, Rian D.; Bourg, Jean-Baptiste
  • Angewandte Chemie International Edition, Vol. 46, Issue 16
  • DOI: 10.1002/anie.200605083

CuH in a Bottle: A Convenient Reagent for Asymmetric Hydrosilylations
journal, October 2005


Stable Silver(I) Hydride Complexes Supported by Diselenophosphate Ligands
journal, January 2010

  • Liu, C. W.; Chang, Hao-Wei; Sarkar, Bijay
  • Inorganic Chemistry, Vol. 49, Issue 2
  • DOI: 10.1021/ic901408n

Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference
journal, September 2005

  • Lavallo, Vincent; Canac, Yves; Präsang, Carsten
  • Angewandte Chemie International Edition, Vol. 44, Issue 35, p. 5705-5709
  • DOI: 10.1002/anie.200501841

A dinuclear silver hydride and an umpolung reaction of CO2
journal, January 2013

  • Tate, Brandon K.; Wyss, Chelsea M.; Bacsa, John
  • Chemical Science, Vol. 4, Issue 8
  • DOI: 10.1039/c3sc50896j

Coinage Metal Hydrides: Synthesis, Characterization, and Reactivity
journal, June 2016


Facile Synthesis of Silver(I)−Carbene Complexes. Useful Carbene Transfer Agents
journal, March 1998

  • Wang, Harrison M. J.; Lin, Ivan J. B.
  • Organometallics, Vol. 17, Issue 5
  • DOI: 10.1021/om9709704

CuH-Catalyzed Reactions
journal, August 2008

  • Deutsch, Carl; Krause, Norbert; Lipshutz, Bruce H.
  • Chemical Reviews, Vol. 108, Issue 8
  • DOI: 10.1021/cr0684321

Hydrogen-carbon-13 spin-spin coupling in transition metal hydride complexes
journal, August 1969

  • Whitesides, George M.; Maglio, G.
  • Journal of the American Chemical Society, Vol. 91, Issue 18
  • DOI: 10.1021/ja01046a006

Preparation and crystallographic characterization of a hexameric triphenylphosphinecopper hydride cluster
journal, April 1971

  • Bezman, Susan A.; Churchill, Melvyn R.; Osborn, John A.
  • Journal of the American Chemical Society, Vol. 93, Issue 8
  • DOI: 10.1021/ja00737a045

Nucleophilic T-Shaped (LXL)Au(I)-Pincer Complexes: Protonation and Alkylation
journal, December 2016

  • Kleinhans, George; Hansmann, Max M.; Guisado-Barrios, Gregorio
  • Journal of the American Chemical Society, Vol. 138, Issue 49
  • DOI: 10.1021/jacs.6b11359

Experimental and Computational Studies of the Copper Borate Complexes [(NHC)Cu(HBEt 3 )] and [(NHC)Cu(HB(C 6 F 5 ) 3 )]
journal, November 2016

  • Collins, Lee R.; Rajabi, Nasir A.; Macgregor, Stuart A.
  • Angewandte Chemie, Vol. 128, Issue 50
  • DOI: 10.1002/ange.201608081

Synthesis and Reactivity of New Copper(I) Hydride Dimers
journal, February 2016


Bonding and Reactivity of a μ-Hydrido Dicopper Cation
journal, October 2013

  • Wyss, Chelsea M.; Tate, Brandon K.; Bacsa, John
  • Angewandte Chemie, Vol. 125, Issue 49
  • DOI: 10.1002/ange.201306736

Singlet (Phosphino)phosphinidenes are Electrophilic
journal, June 2016

  • Hansmann, Max M.; Jazzar, Rodolphe; Bertrand, Guy
  • Journal of the American Chemical Society, Vol. 138, Issue 27
  • DOI: 10.1021/jacs.6b04232

Generalization of the Copper to Late-Transition-Metal Transmetallation to Carbenes beyond N-Heterocyclic Carbenes
journal, May 2016

  • Bidal, Yannick D.; Santoro, Orlando; Melaimi, Mohand
  • Chemistry - A European Journal, Vol. 22, Issue 27
  • DOI: 10.1002/chem.201601254

Intramolecular “Hydroiminiumation and -amidiniumation” of Alkenes:  A Convenient, Flexible, and Scalable Route to Cyclic Iminium and Imidazolinium Salts
journal, April 2007

  • Jazzar, Rodolphe; Bourg, Jean-Baptiste; Dewhurst, Rian D.
  • The Journal of Organic Chemistry, Vol. 72, Issue 9
  • DOI: 10.1021/jo0703909

Copper(I) carbene hydride complexes acting both as reducing agent and precursor for Cu ALD: a study through density functional theory
journal, November 2013


A Singlet Phosphinidene Stable at Room Temperature
journal, July 2016


Reactions of a Stable Monomeric Gold(I) Hydride Complex
journal, November 2008

  • Tsui, Emily Y.; Müller, Peter; Sadighi, Joseph P.
  • Angewandte Chemie, Vol. 120, Issue 46
  • DOI: 10.1002/ange.200803842

Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane
journal, January 2017

  • Romero, Erik A.; Jazzar, Rodolphe; Bertrand, Guy
  • Chemical Science, Vol. 8, Issue 1
  • DOI: 10.1039/C6SC02668K

Stable Carbenes: From ‘Laboratory Curiosities' to Catalysis Mainstays
journal, June 2013


Ancillary ligand-free copper catalysed hydrohydrazination of terminal alkynes with NH 2 NH 2
journal, January 2016

  • Peltier, Jesse L.; Jazzar, Rodolphe; Melaimi, Mohand
  • Chemical Communications, Vol. 52, Issue 13
  • DOI: 10.1039/C5CC10427K

Carbenes Introduction
journal, August 2009

  • Arduengo, Anthony J.; Bertrand, Guy
  • Chemical Reviews, Vol. 109, Issue 8
  • DOI: 10.1021/cr900241h

NHC–copper hydrides as chemoselective reducing agents: catalytic reduction of alkynes, alkyl triflates, and alkyl halides
journal, July 2014


Stable singlet carbenes as mimics for transition metal centers
journal, January 2011

  • Martin, David; Soleilhavoup, Michele; Bertrand, Guy
  • Chem. Sci., Vol. 2, Issue 3
  • DOI: 10.1039/C0SC00388C

Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne “click reaction”
journal, June 2015

  • Jin, Liqun; Tolentino, Daniel R.; Melaimi, Mohand
  • Science Advances, Vol. 1, Issue 5
  • DOI: 10.1126/sciadv.1500304

Synthesis of a Room-Temperature-Stable Dimeric Copper(I) Hydride
journal, October 2010

  • Frey, Guido D.; Donnadieu, Bruno; Soleilhavoup, Michele
  • Chemistry - An Asian Journal, Vol. 6, Issue 2
  • DOI: 10.1002/asia.201000576

Selective hydride-mediated conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds using [(Ph3P)CuH]6
journal, January 1988

  • Mahoney, Wayne S.; Brestensky, Donna M.; Stryker, Jeffrey M.
  • Journal of the American Chemical Society, Vol. 110, Issue 1
  • DOI: 10.1021/ja00209a048

A Thermally Stable Gold(III) Hydride: Synthesis, Reactivity, and Reductive Condensation as a Route to Gold(II) Complexes
journal, September 2012

  • Roşca, Dragoş-Adrian; Smith, Dan A.; Hughes, David L.
  • Angewandte Chemie International Edition, Vol. 51, Issue 42
  • DOI: 10.1002/anie.201206468

Fire and Ice: A Gold(III) Monohydride
journal, November 2012

  • Hashmi, A. Stephen K.
  • Angewandte Chemie International Edition, Vol. 51, Issue 52
  • DOI: 10.1002/anie.201208603

(CAAC)CuX-catalyzed hydroboration of terminal alkynes with pinacolborane directed by the X-ligand
journal, February 2017


Bonding and Reactivity of a μ-Hydrido Dicopper Cation
journal, October 2013

  • Wyss, Chelsea M.; Tate, Brandon K.; Bacsa, John
  • Angewandte Chemie International Edition, Vol. 52, Issue 49
  • DOI: 10.1002/anie.201306736

Lewis-base adducts of Group 11 metal(I) compounds. 49. Structural characterization of hexameric and pentameric (triphenylphosphine)copper(I) hydrides
journal, April 1989

  • Albert, Candiera F.; Healy, Peter C.; Kildea, John D.
  • Inorganic Chemistry, Vol. 28, Issue 7
  • DOI: 10.1021/ic00306a019

Development of N-Heterocyclic Carbene–Copper Complexes for 1,3-Halogen Migration
journal, August 2015


Intramolecular “Hydroiminiumation” of Alkenes: Application to the Synthesis of Conjugate Acids of Cyclic Alkyl Amino Carbenes (CAACs)
journal, April 2007

  • Jazzar, Rodolphe; Dewhurst, Rian D.; Bourg, Jean-Baptiste
  • Angewandte Chemie, Vol. 119, Issue 16
  • DOI: 10.1002/ange.200605083

Kupfer- und Silber-Carbenkomplexe ohne Heteroatom-Stabilisierung: Struktur, Spektroskopie und relativistische Effekte
journal, July 2015

  • Hussong, Matthias W.; Hoffmeister, Wilhelm T.; Rominger, Frank
  • Angewandte Chemie, Vol. 127, Issue 35
  • DOI: 10.1002/ange.201504117

Reactions of a Stable Monomeric Gold(I) Hydride Complex
journal, November 2008

  • Tsui, Emily Y.; Müller, Peter; Sadighi, Joseph P.
  • Angewandte Chemie International Edition, Vol. 47, Issue 46
  • DOI: 10.1002/anie.200803842

Mechanistic Insight into the (NHC)copper(I)-Catalyzed Hydrosilylation of Ketones
journal, April 2014

  • Vergote, Thomas; Nahra, Fady; Merschaert, Alain
  • Organometallics, Vol. 33, Issue 8
  • DOI: 10.1021/om401097q

Isolation of Neutral Mononuclear Copper Complexes Stabilized by Two Cyclic (Alkyl)(amino)carbenes
journal, April 2014

  • Weinberger, David S.; Amin SK, Nurul; Mondal, Kartik Chandra
  • Journal of the American Chemical Society, Vol. 136, Issue 17
  • DOI: 10.1021/ja502521b

Copper(I) Complexes Bearing Carbenes Beyond Classical N-Heterocyclic Carbenes: Synthesis and Catalytic Activity in “Click Chemistry”
journal, October 2015

  • Bidal, Yannick D.; Lesieur, Mathieu; Melaimi, Mohand
  • Advanced Synthesis & Catalysis, Vol. 357, Issue 14-15
  • DOI: 10.1002/adsc.201500453

Preparation and application of N-heterocyclic carbene complexes of Ag(I)
journal, March 2007


Gold-Katalyse
journal, December 2006

  • Hashmi, A. Stephen K.; Hutchings, Graham J.
  • Angewandte Chemie, Vol. 118, Issue 47
  • DOI: 10.1002/ange.200602454

Copper and Silver Carbene Complexes without Heteroatom-Stabilization: Structure, Spectroscopy, and Relativistic Effects
journal, July 2015

  • Hussong, Matthias W.; Hoffmeister, Wilhelm T.; Rominger, Frank
  • Angewandte Chemie International Edition, Vol. 54, Issue 35
  • DOI: 10.1002/anie.201504117

CuH in a Bottle: A Convenient Reagent for Asymmetric Hydrosilylations
journal, October 2005

  • Lipshutz, Bruce H.; Frieman, Bryan A.
  • Angewandte Chemie International Edition, Vol. 44, Issue 39
  • DOI: 10.1002/anie.200500800