Dicopper Cu(I)Cu(I) and Cu(I)Cu(II) Complexes in Copper-Catalyzed Azide–Alkyne Cycloaddition

Ziegler, Micah S.; Lakshmi, K. V.; Tilley, T. Don

doi:10.1021/jacs.6b13261

Title: Dicopper Cu(I)Cu(I) and Cu(I)Cu(II) Complexes in Copper-Catalyzed Azide–Alkyne Cycloaddition

Journal Article · Mon Apr 10 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b13261· OSTI ID:1476482

^[1]; Lakshmi, K. V. ^[2]; Tilley, T. Don ^[1]

Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
Rensselaer Polytechnic Inst., Troy, NY (United States). Dept. of Chemistry and Chemical Biology. The Baruch ’60 Center for Biochemical Solar Energy Research

Here, a discrete, dicopper μ-alkynyl complex, [Cu₂(μ-η¹:η¹-C≡C(C₆H₄)CH₃)DPFN]NTf₂ (DPFN = 2,7-bis(fluoro-di(2-pyridyl)methyl)-1,8-naphthyridine; NTf₂^– = N(SO₂CF₃)₂^–), reacts with p-tolylazide to yield a dicopper complex with a symmetrically bridging 1,2,3-triazolide, [Cu₂(μ-η¹:η¹-(1,4-bis(4-tolyl)-1,2,3-triazolide))DPFN]NTf₂. This transformation exhibits bimolecular reaction kinetics and represents a key step in a proposed, bimetallic mechanism for copper-catalyzed azide–alkyne cycloaddition (CuAAC). The μ-alkynyl and μ-triazolide complexes undergo reversible redox events (by cyclic voltammetry), suggesting that a cycloaddition pathway involving mixed-valence dicopper species might also be possible. Synthesis and characterization of the mixed-valence μ-alkynyl dicopper complex, [Cu₂(μ-η¹:η¹-C≡C(C₆H₄)CH₃)DPFN](NTf₂)₂, revealed an electronic structure with an unexpected partially delocalized spin, as evidenced by electron paramagnetic resonance spectroscopy. Finally, studies of the mixed-valence μ-alkynyl complex’s reactivity suggest that a mixed-valence pathway is less likely than one involving intermediates with only copper(I).

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Inst. of Health (NIH) (United States); National Science Foundation (NSF)

Grant/Contract Number:: AC02-05CH11231; FG02-07ER15903; SC0004993; S10-RR027172; SRR023679A; 1S10RR016634-01; GM68933; DGE 1106400

OSTI ID:: 1476482

Journal Information:: Journal of the American Chemical Society, Vol. 139, Issue 15; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (80)

Approaches Towards the Synthesis of Allenyl Azides L'abbé, Gerrit; Mahy, Michel; Bollyn, Marcus Bulletin des Sociétés Chimiques Belges, Vol. 92, Issue 10 https://doi.org/10.1002/bscb.19830921010	journal	September 2010
Are Azidocumulenes Accessible? L'abbé, Gerrit Bulletin des Sociétés Chimiques Belges, Vol. 93, Issue 7 https://doi.org/10.1002/bscb.19840930706	journal	September 2010
Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064 https://doi.org/10.1021/jo011148j	journal	May 2002
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4	journal	July 2002
Click Chemistry: Diverse Chemical Function from a Few Good Reactions Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry Angewandte Chemie International Edition, Vol. 40, Issue 11, p. 2004-2021 https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5	journal	June 2001
Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition Wang, Qian; Chan, Timothy R.; Hilgraf, Robert Journal of the American Chemical Society, Vol. 125, Issue 11, p. 3192-3193 https://doi.org/10.1021/ja021381e	journal	March 2003
The growing impact of click chemistry on drug discovery Kolb, Hartmuth C.; Sharpless, K. Barry Drug Discovery Today, Vol. 8, Issue 24, p. 1128-1137 https://doi.org/10.1016/S1359-6446(03)02933-7	journal	December 2003
Advances in cycloaddition polymerizations Goodall, Glenn W.; Hayes, Wayne Chem. Soc. Rev., Vol. 35, Issue 3 https://doi.org/10.1039/B507209N	journal	January 2006
‘Click’ Chemistry in Polymer and Materials Science Binder, Wolfgang H.; Sachsenhofer, Robert Macromolecular Rapid Communications, Vol. 28, Issue 1 https://doi.org/10.1002/marc.200600625	journal	January 2007
1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science Lutz, Jean-François Angewandte Chemie International Edition, Vol. 46, Issue 7 https://doi.org/10.1002/anie.200604050	journal	February 2007
Bringing Efficiency to Materials Synthesis: The Philosophy of Click Chemistry Hawker, Craig J.; Fokin, Valery V.; Finn, M. G. Australian Journal of Chemistry, Vol. 60, Issue 6 https://doi.org/10.1071/CH07107	journal	January 2007
The growing applications of click chemistry Moses, John E.; Moorhouse, Adam D. Chem. Soc. Rev., Vol. 36, Issue 8 https://doi.org/10.1039/B613014N	journal	January 2007
Polymer “Clicking” by CuAAC Reactions Meldal, Morten Macromolecular Rapid Communications, Vol. 29, Issue 12–13 https://doi.org/10.1002/marc.200800159	journal	July 2008
Cu-Catalyzed Azide−Alkyne Cycloaddition Meldal, Morten; Tornøe, Christian Wenzel Chemical Reviews, Vol. 108, Issue 8 https://doi.org/10.1021/cr0783479	journal	August 2008
Click chemistry: function follows form Finn, M. G.; Fokin, Valery V. Chemical Society Reviews, Vol. 39, Issue 4 https://doi.org/10.1039/c003740k	journal	January 2010
Alkyne-Azide Reactions Schoffelen, Shane; Meldal, Morten Modern Alkyne Chemistry: Catalytic and Atom‐Economic Transformations https://doi.org/10.1002/9783527677894.ch5	book	October 2014
CuAAC: An Efficient Click Chemistry Reaction on Solid Phase Castro, Vida; Rodríguez, Hortensia; Albericio, Fernando ACS Combinatorial Science, Vol. 18, Issue 1 https://doi.org/10.1021/acscombsci.5b00087	journal	December 2015
When CuAAC 'Click Chemistry' goes heterogeneous Chassaing, S.; Bénéteau, V.; Pale, P. Catalysis Science & Technology, Vol. 6, Issue 4 https://doi.org/10.1039/C5CY01847A	journal	January 2016
Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates Himo, Fahmi; Lovell, Timothy; Hilgraf, Robert Journal of the American Chemical Society, Vol. 127, Issue 1 https://doi.org/10.1021/ja0471525	journal	January 2005
Mechanism of the Ligand-Free CuI-Catalyzed Azide-Alkyne Cycloaddition Reaction Rodionov, Valentin O.; Fokin, Valery V.; Finn, M. G. Angewandte Chemie International Edition, Vol. 44, Issue 15 https://doi.org/10.1002/anie.200461496	journal	April 2005
Cu ^I ‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective Bock, Victoria D.; Hiemstra, Henk; van Maarseveen, Jan H. European Journal of Organic Chemistry, Vol. 2006, Issue 1 https://doi.org/10.1002/ejoc.200500483	journal	December 2005
Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition Rodionov, Valentin O.; Presolski, Stanislav I.; Gardinier, Sean Journal of the American Chemical Society, Vol. 129, Issue 42 https://doi.org/10.1021/ja072678l	journal	October 2007
Ligand-Accelerated Cu-Catalyzed Azide−Alkyne Cycloaddition: A Mechanistic Report Rodionov, Valentin O.; Presolski, Stanislav I.; Díaz Díaz, David Journal of the American Chemical Society, Vol. 129, Issue 42 https://doi.org/10.1021/ja072679d	journal	October 2007
Tailored Ligand Acceleration of the Cu-Catalyzed Azide−Alkyne Cycloaddition Reaction: Practical and Mechanistic Implications Presolski, Stanislav I.; Hong, Vu; Cho, So-Hye Journal of the American Chemical Society, Vol. 132, Issue 41 https://doi.org/10.1021/ja105743g	journal	October 2010
Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(i) acetylides Hein, Jason E.; Fokin, Valery V. Chemical Society Reviews, Vol. 39, Issue 4 https://doi.org/10.1039/b904091a	journal	January 2010
Mechanistic Investigations of Copper(I)-Catalysed Alkyne–Azide Cycloaddition Reactions Buckley, Benjamin R.; Heaney, Harry Topics in Heterocyclic Chemistry https://doi.org/10.1007/7081_2011_71	book	January 2012
Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition Berg, Regina; Straub, Bernd F. Beilstein Journal of Organic Chemistry, Vol. 9 https://doi.org/10.3762/bjoc.9.308	journal	January 2013
Reaction mechanisms of transition-metal-catalyzed azide–alkyne cycloaddition “click” reactions: A DFT investigation Ikhlef, Djamila; Wang, Changlong; Kahlal, Samia Computational and Theoretical Chemistry, Vol. 1073 https://doi.org/10.1016/j.comptc.2015.09.020	journal	December 2015
Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends Wang, Changlong; Ikhlef, Djamila; Kahlal, Samia Coordination Chemistry Reviews, Vol. 316 https://doi.org/10.1016/j.ccr.2016.02.010	journal	June 2016
NMR and DFT Study of the Copper(I)-Catalyzed Cycloaddition Reaction: H/D Scrambling of Alkynes and Variable Reaction Order of the Catalyst Kalvet, Indrek; Tammiku-Taul, Jaana; Mäeorg, Uno ChemCatChem, Vol. 8, Issue 10 https://doi.org/10.1002/cctc.201600176	journal	April 2016
A DFT Study on the Binuclear CuAAC Reaction: Mechanism in Light of New Experiments Özkılıç, Yılmaz; Tüzün, Nurcan Ş. Organometallics, Vol. 35, Issue 16 https://doi.org/10.1021/acs.organomet.6b00279	journal	July 2016
Isolation of a Copper(I) Triazolide: A “Click” Intermediate Nolte, Christoph; Mayer, Peter; Straub, Bernd F. Angewandte Chemie International Edition, Vol. 46, Issue 12 https://doi.org/10.1002/anie.200604444	journal	March 2007
Alkynylcopper(i) polymers and their use in a mechanistic study of alkyne–azide click reactions Buckley, Benjamin R.; Dann, Sandra E.; Harris, Daniel P. Chemical Communications, Vol. 46, Issue 13 https://doi.org/10.1039/b924649e	journal	January 2010
Experimental Evidence for the Involvement of Dinuclear Alkynylcopper(I) Complexes in Alkyne-Azide Chemistry Buckley, Benjamin R.; Dann, Sandra E.; Heaney, Harry Chemistry - A European Journal, Vol. 16, Issue 21 https://doi.org/10.1002/chem.201000447	journal	April 2010
A Fluxional Copper Acetylide Cluster in CuAAC Catalysis Makarem, Ata; Berg, Regina; Rominger, Frank Angewandte Chemie International Edition, Vol. 54, Issue 25 https://doi.org/10.1002/anie.201502368	journal	April 2015
Experimental Investigation on the Mechanism of Chelation-Assisted, Copper(II) Acetate-Accelerated Azide–Alkyne Cycloaddition Kuang, Gui-Chao; Guha, Pampa M.; Brotherton, Wendy S. Journal of the American Chemical Society, Vol. 133, Issue 35 https://doi.org/10.1021/ja203733q	journal	September 2011
Highly Active Dinuclear Copper Catalysts for Homogeneous Azide-Alkyne Cycloadditions Berg, Regina; Straub, Johannes; Schreiner, Ella Advanced Synthesis & Catalysis, Vol. 354, Issue 18 https://doi.org/10.1002/adsc.201200734	journal	November 2012
Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne “click reaction” Jin, Liqun; Tolentino, Daniel R.; Melaimi, Mohand Science Advances, Vol. 1, Issue 5 https://doi.org/10.1126/sciadv.1500304	journal	June 2015
Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science, Vol. 340, Issue 6131 https://doi.org/10.1126/science.1229506	journal	April 2013
Dinuclear Copper Intermediates in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Directly Observed by Electrospray Ionization Mass Spectrometry Iacobucci, Claudio; Reale, Samantha; Gal, Jean-François Angewandte Chemie International Edition, Vol. 54, Issue 10 https://doi.org/10.1002/anie.201410301	journal	January 2015
CuAAC Click Reactions in the Gas Phase: Unveiling the Reactivity of Bis-Copper Intermediates Iacobucci, Claudio; Lebon, Alexandre; De Angelis, Francesco Chemistry - A European Journal, Vol. 22, Issue 52 https://doi.org/10.1002/chem.201603518	journal	November 2016
The Janus Face of the X Ligand in the Copper-Catalyzed Azide–Alkyne Cycloaddition Jin, Liqun; Romero, Erik A.; Melaimi, Mohand Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11028	journal	December 2015
Enhanced Reactivity of Dinuclear Copper(I) Acetylides in Dipolar Cycloadditions Ahlquist, Mårten; Fokin, Valery V. Organometallics, Vol. 26, Issue 18 https://doi.org/10.1021/om700669v	journal	August 2007
µ-Acetylide and µ-alkenylidene ligands in “click” triazole syntheses Straub, Bernd F. Chemical Communications, Issue 37 https://doi.org/10.1039/b706926j	journal	January 2007
Assessing the whole range of CuAAC mechanisms by DFT calculations—on the intermediacy of copper acetylides Cantillo, David; Ávalos, Martín; Babiano, Reyes Organic & Biomolecular Chemistry, Vol. 9, Issue 8 https://doi.org/10.1039/c0ob01001d	journal	January 2011
On the Mechanism of Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Zhu, Lei; Brassard, Christopher J.; Zhang, Xiaoguang The Chemical Record, Vol. 16, Issue 3 https://doi.org/10.1002/tcr.201600002	journal	May 2016
Aryl Group Transfer from Tetraarylborato Anions to an Electrophilic Dicopper(I) Center and Mixed-Valence μ-Aryl Dicopper(I,II) Complexes Ziegler, Micah S.; Levine, Daniel S.; Lakshmi, K. V. Journal of the American Chemical Society, Vol. 138, Issue 20 https://doi.org/10.1021/jacs.6b00802	journal	May 2016
Copper(I) Alkyne and Alkynide Complexes Lang, Heinrich; Jakob, Alexander; Milde, Bianca Organometallics, Vol. 31, Issue 22 https://doi.org/10.1021/om300628g	journal	August 2012
Synthesis and Solid-State Structure of [Cu5(ButC.tplbond.C)2(bpy)4][CF3SO3]3.cntdot.CH2Cl2: An Unusual Cationic Organocopper(I) Complex Held Together by Two Bridging Alkynyl Ligands Reger, Daniel L.; Collins, James E.; Huff, Mark F. Organometallics, Vol. 14, Issue 12 https://doi.org/10.1021/om00012a008	journal	December 1995
Synthesis and reactivity of binuclear copper(I) complexes of 2-(diphenylphosphino)-6-(pyrazol-1-yl)pyridine (L1). Crystal structures of [Cu2(μ-L1)2(MeCN)2][ClO4]2, [Cu2(μ-L1)2(μ-η1-CCPh)][ClO4]· CHCl3·H2O and [Cu2(μ-L1)2(μ-Cl)][ClO4]·H2O Kuang, Shan-Ming; Zhang, Zheng-Zhi; Wang, Qi-Guang Journal of the Chemical Society, Dalton Transactions, Issue 7 https://doi.org/10.1039/a708800k	journal	January 1998
Bonding and Reactivity of a Dicopper(I) μ-Boryl Cation Wyss, Chelsea M.; Bitting, Jamie; Bacsa, John Organometallics, Vol. 35, Issue 2 https://doi.org/10.1021/acs.organomet.5b00961	journal	January 2016
Investigations of Substituent Effects by Nuclear Magnetic Resonance Spectroscopy and All-valence Electron Molecular Orbital Calculations. IV. 4-Substituted Phenylacetylenes Dawson, Daniel A.; Reynolds, William F. Canadian Journal of Chemistry, Vol. 53, Issue 3 https://doi.org/10.1139/v75-053	journal	February 1975
Rationalizing the Catalytic Activity of Copper in the Cycloaddition of Azide and Alkynes (CuAAC) with the Topology of ∇²ρ(r) and ∇∇²ρ(r) Calvo-Losada, Saturnino; Pino-González, María Soledad; Quirante, José Joaquín The Journal of Physical Chemistry B, Vol. 119, Issue 4 https://doi.org/10.1021/jp5055414	journal	January 2015
Intervalence Charge Transfer (IVCT) in Trinuclear and Tetranuclear Complexes of Iron, Ruthenium, and Osmium D'Alessandro, Deanna M.; Keene, F. Richard Chemical Reviews, Vol. 106, Issue 6 https://doi.org/10.1021/cr050010o	journal	June 2006
Mixed Valence Chemistry-A Survey and Classification Robin, Melvin B.; Day, Peter Advances in Inorganic Chemistry and Radiochemistry https://doi.org/10.1016/S0065-2792(08)60179-X	book	January 1968
Binuclear complexes of macrocyclic ligands. A mixed-valence copper(II)-copper(I) complex which exhibits unusual temperature-dependent behavior Gagne, Robert R.; Koval, Carl A.; Smith, Thomas J. Journal of the American Chemical Society, Vol. 99, Issue 25 https://doi.org/10.1021/ja00467a067	journal	December 1977
Intramolecular electron transfer in a series of mixed-valence copper(II)-copper(I) complexes Long, Russell C.; Hendrickson, David N. Journal of the American Chemical Society, Vol. 105, Issue 6 https://doi.org/10.1021/ja00344a018	journal	March 1983
Detailed spectroscopic analysis of half-met hemocyanins: mixed-valent contributions to electronic properties and structure Westmoreland, T. David; Wilcox, Dean E.; Baldwin, Michael J. Journal of the American Chemical Society, Vol. 111, Issue 16 https://doi.org/10.1021/ja00198a019	journal	August 1989
Localization and Delocalization in a Mixed-Valence Dicopper Helicate Jeffery, John C.; Riis-Johannessen, Thomas; Anderson, Callum J. Inorganic Chemistry, Vol. 46, Issue 7 https://doi.org/10.1021/ic061504m	journal	February 2007
One-electron redox processes at binuclear copper centers Addison, A. W. Inorganic and Nuclear Chemistry Letters, Vol. 12, Issue 12 https://doi.org/10.1016/0020-1650(76)80004-9	journal	January 1976
Synthesis, structure, and electrochemistry of a novel macrocyclic dicopper(II) complex. Four one-electron-transfer steps producing binuclear copper(III) and copper(I) species and mixed-valence-state species Mandal, Sanat K.; Thompson, Laurence K.; Nag, Kamalaksha Inorganic Chemistry, Vol. 26, Issue 9 https://doi.org/10.1021/ic00256a012	journal	May 1987
Dinuclear copper(II), nickel(II) and mixed valence CuII-CuI complexes: influence of donor groups on redox behaviour of dicopper complexes Srinivas, B.; Zacharias, P. S. Polyhedron, Vol. 11, Issue 15 https://doi.org/10.1016/S0277-5387(00)83744-4	journal	January 1992
Crystallographic, spectroscopic and theoretical studies of an electron-deiocalized Cu(1.5)–Cu(1.5) complex Barr, Mary E.; Smith, Paul H.; Antholine, William E. J. Chem. Soc., Chem. Commun., Issue 21 https://doi.org/10.1039/C39930001649	journal	January 1993
Synthesis and Characterization of Spin-Delocalized Carboxylate-Bridged Cu(I)−Cu(II) Mixed-Valence Complexes Having Only Oxygen Donor Ligands LeCloux, Daniel D.; Davydov, Roman; Lippard, Stephen J. Journal of the American Chemical Society, Vol. 120, Issue 27 https://doi.org/10.1021/ja9805021	journal	June 1998
A copper–copper bond by intent Harding, Charles; Nelson, Jane; Symons, Martyn C. R. J. Chem. Soc., Chem. Commun., Issue 21 https://doi.org/10.1039/C39940002499	journal	January 1994
Synthesis and Characterization of Several Dicopper(I) Complexes and a Spin-Delocalized Dicopper(I,II) Mixed-Valence Complex Using a 1,8-Naphthyridine-Based Dinucleating Ligand He, Chuan; Lippard, Stephen J. Inorganic Chemistry, Vol. 39, Issue 23 https://doi.org/10.1021/ic0005339	journal	October 2000
Synthesis and Characterization of Completely Delocalized Mixed-Valent Dicopper Complexes Gupta, Rajeev; Zhang, Zhi Hui; Powell, Douglas Inorganic Chemistry, Vol. 41, Issue 20 https://doi.org/10.1021/ic0202918	journal	September 2002
Dicopper(i,i) and delocalized mixed-valent dicopper(i,ii) complexes of a sterically hindered carboxylate ligand Hagadorn, John R.; Zahn, Theresa I.; Que, Jr., Lawrence Dalton Transactions, Issue 9 https://doi.org/10.1039/b301154b	journal	March 2003
Binuclear complexes of macrocyclic ligands. Electrochemical and spectral properties of homobinuclear CuIICuII, CuIICuI, and CuICuI species including an estimated intramolecular electron transfer rate Gagne, Robert R.; Koval, Carl A.; Smith, Thomas J. Journal of the American Chemical Society, Vol. 101, Issue 16 https://doi.org/10.1021/ja00510a023	journal	August 1979
Dinuclear copper(II) and mixed-valence copper(II)-copper(I) complexes of 34-membered macrocyclic ligands (H2M1, H2M2) capable of forming endogenous phenolate and pyridazino bridges. X-ray crystal structures of the dinuclear copper(II) complexes [Cu2M1][BF4]2.cntdot.H2O and [Cu2M2][BF4]2.cntdot.CH3OH, which exhibit a remarkable ligand twist Tandon, Santokh S.; Thompson, Laurence K.; Bridson, John N. Inorganic Chemistry, Vol. 32, Issue 1 https://doi.org/10.1021/ic00053a006	journal	January 1993
Binuclear mixed-valence copper acetate complex as a model for copper-copper interaction in enzymes Sigwart, C.; Hemmerich, Peter; Spence, Jack T. Inorganic Chemistry, Vol. 7, Issue 12 https://doi.org/10.1021/ic50070a015	journal	December 1968
Structural, magnetic, and electrochemical studies on macrocyclic dicopper(II) complexes with varying chelate ring size Mandal, Sanat K.; Thompson, Laurence K.; Newlands, Michael J. Inorganic Chemistry, Vol. 28, Issue 19 https://doi.org/10.1021/ic00318a020	journal	September 1989
A Thiolate-Bridged, Fully Delocalized Mixed-Valence Dicopper(I,II) Complex That Models the Cu_A Biological Electron-Transfer Site Houser, Robert P.; Young, Victor G.; Tolman, William B. Journal of the American Chemical Society, Vol. 118, Issue 8 https://doi.org/10.1021/ja953776m	journal	January 1996
Mixed-Valence Cu^I−Cu^II and Heterodimetallic Cu^I−M^II Bis(carboxylate-bridged) Complexes: Structural, Electrochemical, and Spectroscopic Investigations LeCloux, Daniel D.; Davydov, Roman; Lippard, Stephen J. Inorganic Chemistry, Vol. 37, Issue 26 https://doi.org/10.1021/ic980763b	journal	December 1998
Amido-Bridged Cu ₂ N ₂ Diamond Cores that Minimize Structural Reorganization and Facilitate Reversible Redox Behavior between a Cu ¹ Cu ¹ and a Class III Delocalized Cu ^1.5 Cu ^1.5 Species Harkins, Seth B.; Peters, Jonas C. Journal of the American Chemical Society, Vol. 126, Issue 9 https://doi.org/10.1021/ja037364m	journal	March 2004
Synthesis and Characterization of Copper Complexes with Cu ^I Cu ^I , Cu ^1.5 Cu ^1.5 m and Cu ^II Cu ^II Core Structures Supported by a Flexible Dipyridylamide Ligand McMoran, Ethan P.; Powell, Douglas R.; Perez, Felio Inorganic Chemistry, Vol. 55, Issue 21 https://doi.org/10.1021/acs.inorgchem.6b02006	journal	October 2016
EPR Spectra of Active Sites in Copper Proteins Solomon, Edward I.; Gewirth, Andrew A.; Westmoreland, T. David Advanced EPR https://doi.org/10.1016/B978-0-444-88050-5.50030-6	book	January 1989
Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry Hong, Vu; Steinmetz, Nicole F.; Manchester, Marianne Bioconjugate Chemistry, Vol. 21, Issue 10 https://doi.org/10.1021/bc100272z	journal	October 2010
Reliable and Efficient Procedures for the Conjugation of Biomolecules through Huisgen Azide-Alkyne Cycloadditions Lallana, Enrique; Riguera, Ricardo; Fernandez-Megia, Eduardo Angewandte Chemie International Edition, Vol. 50, Issue 38 https://doi.org/10.1002/anie.201101019	journal	August 2011
Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling Uttamapinant, Chayasith; Tangpeerachaikul, Anupong; Grecian, Scott Angewandte Chemie International Edition, Vol. 51, Issue 24 https://doi.org/10.1002/anie.201108181	journal	May 2012

Linked Research (3)

Similar Records

Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex

Journal Article · Thu Dec 19 00:00:00 EST 2019 · Chemical Science · OSTI ID:1476482

Nicolay, Amélie; Ziegler, Micah S.; Small, David W.; +3 more

Robust dicopper( i ) μ-boryl complexes supported by a dinucleating naphthyridine-based ligand

Journal Article · Tue Jun 07 00:00:00 EDT 2022 · Chemical Science · OSTI ID:1476482

Ríos, Pablo; See, Matthew S.; Handford, Rex C.; +2 more

Binding, Release and Functionalization of Intact Pnictogen Tetrahedra Coordinated to Dicopper Complexes

Journal Article · Mon May 16 00:00:00 EDT 2022 · Chemistry - A European Journal · OSTI ID:1476482

Piesch, Martin; Nicolay, Amélie; Haimerl, Maria; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1524417: Experimental Crystal Structure Determination Ziegler, Micah S.; Lakshmi, K. V.; Tilley, T. Don https://doi.org/10.5517/ccdc.csd.cc1n58rv The current record is supplemented by this dataset	dataset	January 2017
CCDC 1524418: Experimental Crystal Structure Determination Ziegler, Micah S.; Lakshmi, K. V.; Tilley, T. Don https://doi.org/10.5517/ccdc.csd.cc1n58sw The current record is supplemented by this dataset	dataset	January 2017
CCDC 1524419: Experimental Crystal Structure Determination Ziegler, Micah S.; Lakshmi, K. V.; Tilley, T. Don https://doi.org/10.5517/ccdc.csd.cc1n58tx The current record is supplemented by this dataset	dataset	January 2017

Title: Dicopper Cu(I)Cu(I) and Cu(I)Cu(II) Complexes in Copper-Catalyzed Azide–Alkyne Cycloaddition

Citation Formats

References (80)

Linked Research (3)

Similar Records

Related Subjects