Why Two Metals Are Better Than One for Heterodinuclear Cobalt–Zirconium-Catalyzed Kumada Coupling

Coombs, Jimmy; Perry, Dalton; Kwon, Doo-Hyun; Thomas, Christine M.; Ess, Daniel H.

doi:10.1021/acs.organomet.8b00449

Title: Why Two Metals Are Better Than One for Heterodinuclear Cobalt–Zirconium-Catalyzed Kumada Coupling

Journal Article · 07 November 2018 · Organometallics

DOI: https://doi.org/10.1021/acs.organomet.8b00449 · OSTI ID:1524783

Coombs, Jimmy ^[1]; Perry, Dalton ^[2]; Kwon, Doo-Hyun ^[2];

^[3];

^[2]

Brigham Young Univ., Provo, UT (United States); Ohio State University
Brigham Young Univ., Provo, UT (United States)
The Ohio State Univ., Columbus, OH (United States)

Heterodinuclear transition metal complexes with a direct metal–metal interaction offer the potential of unique reactivity compared with mononuclear catalysts. Heterodinuclear Co–Zr complexes with phosphinoamide ligands bridging Co and Zr metal centers are effective precatalysts for Kumada C–C bond coupling reactions between alkyl halides and alkyl Grignards. On the other hand, the analogous mononuclear Co tris(phosphinoamine) complex without Zr provides very inefficient catalysis. Here we describe density functional theory calculations that reveal the mechanistic and reactivity impact of the Co–Zr metal–metal interaction and phosphinoamide ligands on alkyl halide–alkyl Grignard Kumada coupling catalysis. The Co–Zr interaction enables two-electron reduction of the precatalyst to form an active catalyst, which then allows a low-energy electron-transfer alkyl halide oxidative addition mechanism. The Co–Zr interaction and the phosphinoamide ligands bridging the metal centers provide a dialkyl intermediate with a low-energy C–C bond forming reductive elimination route through a phosphine dissociation pathway, which is not viable for an analogous mononuclear Co complex.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Brandeis Univ., Waltham, MA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: SC0014151

OSTI ID:: 1524783

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 22 Vol. 37; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (85)

Bimetallic catalysis for C–C and C–X coupling reactions Pye, Dominic R.; Mankad, Neal P. Chemical Science, Vol. 8, Issue 3 https://doi.org/10.1039/C6SC05556G	journal	January 2017
Cobalt‐Catalyzed Cross‐Coupling Reaction between Functionalized Primary and Secondary Alkyl Halides and Aliphatic Grignard Reagents Cahiez, Gérard; Chaboche, Christophe; Duplais, Christophe Advanced Synthesis & Catalysis, Vol. 350, Issue 10 https://doi.org/10.1002/adsc.200800166	journal	July 2008
Catalytic Hydrosilylation of Ketones Using a Co/Zr Heterobimetallic Complex: Evidence for an Unusual Mechanism Involving Ketyl Radicals Zhou, Wen; Marquard, Seth L.; Bezpalko, Mark W. Organometallics, Vol. 32, Issue 6 https://doi.org/10.1021/om301194g	journal	February 2013
Metal–Metal Bonding in Low-Coordinate Dicobalt Complexes Supported by Phosphinoamide Ligands Mathialagan, Ramyaa; Kuppuswamy, Subramaniam; De Denko, Alexandra T. Inorganic Chemistry, Vol. 52, Issue 2 https://doi.org/10.1021/ic3018375	journal	January 2013
Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formation Kattamuri, Padmanabha V.; Yin, Jun; Siriwongsup, Surached Journal of the American Chemical Society, Vol. 139, Issue 32 https://doi.org/10.1021/jacs.7b05279	journal	July 2017
Activation of CO ₂ by a Heterobimetallic Zr/Co Complex Krogman, Jeremy P.; Foxman, Bruce M.; Thomas, Christine M. Journal of the American Chemical Society, Vol. 133, Issue 37 https://doi.org/10.1021/ja2071847	journal	September 2011
Computationally Guided Discovery of a Catalytic Cobalt-Decorated Metal–Organic Framework for Ethylene Dimerization Bernales, Varinia; League, Aaron B.; Li, Zhanyong The Journal of Physical Chemistry C, Vol. 120, Issue 41 https://doi.org/10.1021/acs.jpcc.6b07362	journal	October 2016
Synthesis of chiral heterobimetallic tris(phosphinoamide) Zr/Co complexes Saper, Noam I.; Bezpalko, Mark W.; Foxman, Bruce M. Polyhedron, Vol. 114 https://doi.org/10.1016/j.poly.2015.11.001	journal	August 2016
Synthesis, Structure, and Reactivity of an Anionic Zr–Oxo Relevant to CO ₂ Reduction by a Zr/Co Heterobimetallic Complex Krogman, Jeremy P.; Bezpalko, Mark W.; Foxman, Bruce M. Inorganic Chemistry, Vol. 52, Issue 6 https://doi.org/10.1021/ic302473j	journal	February 2013
Structure and Reactivity of Early−Late Heterobimetallic Complexes ^† Wheatley, Nigel; Kalck, Philippe Chemical Reviews, Vol. 99, Issue 12 https://doi.org/10.1021/cr980325m	journal	December 1999
Cobalt-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Allylic and Benzylic Grignard Reagents and Their Application to Tandem Radical Cyclization/Cross-Coupling Reactions Ohmiya, Hirohisa; Tsuji, Takashi; Yorimitsu, Hideki Chemistry - A European Journal, Vol. 10, Issue 22 https://doi.org/10.1002/chem.200400545	journal	November 2004
Bimetallic Oxidative Addition in Nickel-Catalyzed Alkyl–Aryl Kumada Coupling Reactions Breitenfeld, Jan; Wodrich, Matthew D.; Hu, Xile Organometallics, Vol. 33, Issue 20 https://doi.org/10.1021/om500506y	journal	June 2014
Selectivity Effects in Bimetallic Catalysis Mankad, Neal P. Chemistry - A European Journal, Vol. 22, Issue 17 https://doi.org/10.1002/chem.201505002	journal	February 2016
35 years of palladium-catalyzed cross-coupling with Grignard reagents: how far have we come? Knappke, Christiane E. I.; Jacobi von Wangelin, Axel Chemical Society Reviews, Vol. 40, Issue 10 https://doi.org/10.1039/c1cs15137a	journal	January 2011
Metal–metal multiple bonded intermediates in catalysis Berry, John F. Journal of Chemical Sciences, Vol. 127, Issue 2 https://doi.org/10.1007/s12039-015-0773-6	journal	February 2015
Mechanistic studies of nickel catalysis in the cross coupling of aryl halides with alkylmetals. Role of arylalkylnickel(II) species as intermediates Morrell, Dennis G.; Kochi, Jay K. Journal of the American Chemical Society, Vol. 97, Issue 25 https://doi.org/10.1021/ja00858a011	journal	December 1975
Mechanism of oxidative addition. Reaction of nickel(0) complexes with aromatic halides Tsou, T. T.; Kochi, J. K. Journal of the American Chemical Society, Vol. 101, Issue 21 https://doi.org/10.1021/ja00515a028	journal	October 1979
Origin of Fast Catalysis in Allylic Amination Reactions Catalyzed by Pd–Ti Heterobimetallic Complexes Walker, Whitney K.; Kay, Benjamin M.; Michaelis, Scott A. Journal of the American Chemical Society, Vol. 137, Issue 23 https://doi.org/10.1021/jacs.5b02428	journal	June 2015
Homo- and hetero-binuclear ansa-metallocenes of the group 4 transition metals as homogeneous co-catalysts for the polymerisation of ethene and propene Yan, Xuefeng; Chernega, Alexander; Green, Malcolm L. H. Journal of Molecular Catalysis A: Chemical, Vol. 128, Issue 1-3 https://doi.org/10.1016/S1381-1169(97)00166-0	journal	February 1998
Catalytic Silylation of Dinitrogen with a Dicobalt Complex Siedschlag, Randall B.; Bernales, Varinia; Vogiatzis, Konstantinos D. Journal of the American Chemical Society, Vol. 137, Issue 14 https://doi.org/10.1021/jacs.5b01445	journal	April 2015
Metal–metal multiple bonding in C3-symmetric bimetallic complexes of the first row transition metals Krogman, Jeremy P.; Thomas, Christine M. Chemical Communications, Vol. 50, Issue 40 https://doi.org/10.1039/c3cc47537a	journal	January 2014
Subtle Differences Between Zr and Hf in Early/Late Heterobimetallic Complexes with Cobalt Setty, Vinay N.; Zhou, Wen; Foxman, Bruce M. Inorganic Chemistry, Vol. 50, Issue 10 https://doi.org/10.1021/ic200445x	journal	May 2011
Cross-Coupling Reaction of Alkyl Halides with Grignard Reagents Catalyzed by Ni, Pd, or Cu Complexes with π-Carbon Ligand(s) Terao, Jun; Kambe, Nobuaki Accounts of Chemical Research, Vol. 41, Issue 11 https://doi.org/10.1021/ar800138a	journal	October 2008
Assignment of the oxidation states of Zr and Co in a highly reactive heterobimetallic Zr/Co complex using X-ray absorption spectroscopy (XANES) Krogman, Jeremy P.; Gallagher, James R.; Zhang, Guanghui Dalton Transactions, Vol. 43, Issue 37 https://doi.org/10.1039/C4DT01534G	journal	January 2014
Structure and reactivity of titanium-platinum and -palladium heterobinuclear complexes with .mu.-methylene ligands Ozawa, Fumiyuki; Park, Joon Won; Mackenzie, Peter B. Journal of the American Chemical Society, Vol. 111, Issue 4 https://doi.org/10.1021/ja00186a026	journal	February 1989
Polymetallic complexes linked to a single-frame ligand: cooperative effects in catalysis Bratko, Ielyzaveta; Gómez, Montserrat Dalton Transactions, Vol. 42, Issue 30 https://doi.org/10.1039/c3dt50963j	journal	January 2013
Proximity and Cooperativity Effects in Binuclear d ⁰ Olefin Polymerization Catalysis. Theoretical Analysis of Structure and Reaction Mechanism Motta, Alessandro; Fragalà, Ignazio L.; Marks, Tobin J. Journal of the American Chemical Society, Vol. 131, Issue 11 https://doi.org/10.1021/ja8077208	journal	March 2009
Metal-Metal Multiple Bonds in Early/Late Heterobimetallic Complexes: Applications Toward Small Molecule Activation and Catalysis Thomas, Christine M. Comments on Inorganic Chemistry, Vol. 32, Issue 1 https://doi.org/10.1080/02603594.2011.593213	journal	January 2011
A Catalytic Application of Co/Zr Heterobimetallic Complexes: Kumada Coupling of Unactivated Alkyl Halides with Alkyl Grignard Reagents Zhou, Wen; Napoline, Jonathan Wesley; Thomas, Christine M. European Journal of Inorganic Chemistry, Vol. 2011, Issue 13 https://doi.org/10.1002/ejic.201100109	journal	March 2011
A First Example of Cobalt-Catalyzed Remote CH Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism Whiteoak, Christopher J.; Planas, Oriol; Company, Anna Advanced Synthesis & Catalysis, Vol. 358, Issue 10 https://doi.org/10.1002/adsc.201600161	journal	April 2016
Mechanistic Considerations for C–C Bond Reductive Coupling at a Cobalt(III) Center Xu, Hongwei; Bernskoetter, Wesley H. Journal of the American Chemical Society, Vol. 133, Issue 38 https://doi.org/10.1021/ja2072548	journal	September 2011
Metal−Metal Multiple Bonds in Early/Late Heterobimetallics Support Unusual Trigonal Monopyramidal Geometries at both Zr and Co Greenwood, Bennett P.; Rowe, Gerard T.; Chen, Chun-Hsing Journal of the American Chemical Society, Vol. 132, Issue 1 https://doi.org/10.1021/ja909310t	journal	January 2010
Configuring Bonds between First-Row Transition Metals Eisenhart, Reed J.; Clouston, Laura J.; Lu, Connie C. Accounts of Chemical Research, Vol. 48, Issue 11 https://doi.org/10.1021/acs.accounts.5b00336	journal	October 2015
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Weigend, Florian; Ahlrichs, Reinhart Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305 https://doi.org/10.1039/b508541a	journal	January 2005
Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G. The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396 https://doi.org/10.1021/jp810292n	journal	May 2009
A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions Zhao, Yan; Truhlar, Donald G. The Journal of Chemical Physics, Vol. 125, Issue 19, Article No. 194101 https://doi.org/10.1063/1.2370993	journal	November 2006
Hydrocarbyl Ligand Transformations on Heterobimetallic Complexes Ritleng, Vincent; Chetcuti, Michael J. Chemical Reviews, Vol. 107, Issue 3 https://doi.org/10.1021/cr940270y	journal	March 2007
Mechanistic insights into cobalt( ii / iii )-catalyzed C–H oxidation: a combined theoretical and experimental study Guo, Xiao-Kang; Zhang, Lin-Bao; Wei, Donghui Chemical Science, Vol. 6, Issue 12 https://doi.org/10.1039/C5SC01807B	journal	January 2015
Scope and mechanism of alkene hydrogenation/isomerization catalyzed by complexes of the type R2E(CH2)2M(CO)(L) (R = Cp, Me, Ph; E = phosphorus, tantalum; M = rhodium, iridium; L = CO, PPh3) Hostetler, Michael J.; Butts, Matthew D.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 115, Issue 7 https://doi.org/10.1021/ja00060a024	journal	April 1993
A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, In Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines Daifuku, Stephanie L.; Al-Afyouni, Malik H.; Snyder, Benjamin E. R. Journal of the American Chemical Society, Vol. 136, Issue 25 https://doi.org/10.1021/ja503596m	journal	June 2014
Syntheses, structure and electrochemical characterization of homo- and heterodinuclear copper complexes with compartmental ligands Zanello, Piero; Tamburini, Sergio; Vigato, Pietro Alessandro Coordination Chemistry Reviews, Vol. 77 https://doi.org/10.1016/0010-8545(87)85034-8	journal	April 1987
Cooperative Catalysis with First-Row Late Transition Metals van der Vlugt, Jarl Ivar; de Bruin, Bas European Journal of Inorganic Chemistry, Vol. 2012, Issue 3, p. 363-375 https://doi.org/10.1002/ejic.201100752	journal	September 2011
Investigation of Ketone C═O Bond Activation Processes by Heterobimetallic Zr/Co and Ti/Co Tris(phosphinoamide) Complexes Zhang, Hongtu; Wu, Bing; Marquard, Seth L. Organometallics, Vol. 36, Issue 18 https://doi.org/10.1021/acs.organomet.7b00445	journal	September 2017
Synthesis and reactivity of Cp2Ta(CH2)2Ir(CO)2: an early-late heterobimetallic complex that catalytically hydrogenates, isomerizes and hydrosilates alkenes Hostetler, Michael J.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 112, Issue 23 https://doi.org/10.1021/ja00179a078	journal	November 1990
The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers Iwasaki, Takanori; Takagawa, Hiroaki; Okamoto, Kanako Synthesis, Vol. 46, Issue 12 https://doi.org/10.1055/s-0033-1341152	journal	May 2014
Catalytic Applications of Early/Late Heterobimetallic Complexes Cooper, Benjamin G.; Napoline, J. Wesley; Thomas, Christine M. Catalysis Reviews, Vol. 54, Issue 1 https://doi.org/10.1080/01614940.2012.619931	journal	January 2012
Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds Gao, Hongyin; Zhou, Zhe; Kwon, Doo-Hyun Nature Chemistry, Vol. 9, Issue 7 https://doi.org/10.1038/nchem.2672	journal	November 2016
Hydroformylation of alkenes and alkynes using a heterobinuclear RhW catalyst Dickson, Ron S.; De Simone, Tania; Campi, Eva M. Inorganica Chimica Acta, Vol. 220, Issue 1-2 https://doi.org/10.1016/0020-1693(94)03871-6	journal	June 1994
Iron Pincer Complexes as Catalysts and Intermediates in Alkyl–Aryl Kumada Coupling Reactions Bauer, Gerald; Wodrich, Matthew D.; Scopelliti, Rosario Organometallics, Vol. 34, Issue 1 https://doi.org/10.1021/om501122p	journal	December 2014
Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi Wadt, Willard R.; Hay, P. Jeffrey The Journal of Chemical Physics, Vol. 82, Issue 1 https://doi.org/10.1063/1.448800	journal	January 1985
A Heterobimetallic Mechanism for C–H Borylation Elucidated from Experimental and Computational Data Parmelee, Sean R.; Mazzacano, Thomas J.; Zhu, Yaqun ACS Catalysis, Vol. 5, Issue 6 https://doi.org/10.1021/acscatal.5b00275	journal	May 2015
Highly Polar Metal-Metal Bonds in “Early-Late” Heterodimetallic Complexes Gade, Lutz H. Angewandte Chemie International Edition, Vol. 39, Issue 15 https://doi.org/10.1002/1521-3773(20000804)39:15<2658::AID-ANIE2658>3.0.CO;2-C	journal	August 2000
Early-late heterobimetallics Stephan, Douglas W. Coordination Chemistry Reviews, Vol. 95, Issue 1 https://doi.org/10.1016/0010-8545(89)80002-5	journal	June 1989
Heterobimetallic compounds linked by heterodifunctional ligands Bullock, R. Morris; Casey, Charles P. Accounts of Chemical Research, Vol. 20, Issue 5 https://doi.org/10.1021/ar00137a002	journal	May 1987
Cobalt-Catalyzed Trimethylsilylmethylmagnesium-Promoted Radical Alkenylation of Alkyl Halides: A Complement to the Heck Reaction Affo, Walter; Ohmiya, Hirohisa; Fujioka, Takuma Journal of the American Chemical Society, Vol. 128, Issue 24 https://doi.org/10.1021/ja061417t	journal	June 2006
Preparation, reactivity, hydroformylation catalysis, and structural studies of the early transition metal/late transition metal heterobimetallic complexes Cp2M(.mu.-PR2)2M'H(CO)PPh3 (M = Zr, Hf; M' = Rh, Ir) Gelmini, Lucio; Stephan, Douglas W. Organometallics, Vol. 7, Issue 4 https://doi.org/10.1021/om00094a010	journal	April 1988
Oxidative addition across Zr/Co multiple bonds in early/late heterobimetallic complexes Thomas, Christine M.; Napoline, J. Wesley; Rowe, Gerard T. Chemical Communications, Vol. 46, Issue 31 https://doi.org/10.1039/c0cc01272f	journal	January 2010
Multielectron Redox Activity Facilitated by Metal−Metal Interactions in Early/Late Heterobimetallics: Co/Zr Complexes Supported by Phosphinoamide Ligands Greenwood, Bennett P.; Forman, Scott I.; Rowe, Gerard T. Inorganic Chemistry, Vol. 48, Issue 13 https://doi.org/10.1021/ic900552b	journal	July 2009
Cobalt-Catalyzed Cross-Coupling Reactions Cahiez, Gérard; Moyeux, Alban Chemical Reviews, Vol. 110, Issue 3 https://doi.org/10.1021/cr9000786	journal	March 2010
Mechanistic investigations of Co(II)-Catalyzed C-N coupling reactions Ahmad, Khalil; Chang, Chun-Ran; Li, Jun Journal of Organometallic Chemistry, Vol. 868 https://doi.org/10.1016/j.jorganchem.2018.05.013	journal	August 2018
Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation: Total Synthesis of (±)-Paroxetine Despiau, Carole F.; Dominey, Andrew P.; Harrowven, David C. European Journal of Organic Chemistry, Vol. 2014, Issue 20 https://doi.org/10.1002/ejoc.201402108	journal	May 2014
Intermetallic Cooperation in Olefin Polymerization Catalyzed by a Binuclear Samarocene Hydride: A Theoretical Study Luo, Gen; Luo, Yi; Hou, Zhaomin Organometallics, Vol. 35, Issue 5 https://doi.org/10.1021/acs.organomet.6b00018	journal	February 2016
Classification of P,N-binucleating ligands for hetero- and homobimetallic complexes Maggini, Simona Coordination Chemistry Reviews, Vol. 253, Issue 13-14 https://doi.org/10.1016/j.ccr.2009.01.030	journal	July 2009
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
N–H activation of hydrazines by a heterobimetallic Zr–Co complex: promotion of one-electron chemistry at Zr Napoline, J. W.; Bezpalko, Mark W.; Foxman, Bruce M. Chem. Commun., Vol. 49, Issue 39 https://doi.org/10.1039/C2CC35594A	journal	January 2013
Synthesis and Investigation of Homo- and Heterobimetallic Ruthenium Olefin Metathesis Catalysts Exhibiting Increased Activities Dias, Eric L.; Grubbs, Robert H. Organometallics, Vol. 17, Issue 13 https://doi.org/10.1021/om9708788	journal	June 1998
Activation of E-H and E-E (E = S, O) Bonds by Heterobimetallic Zr/Co Complexes: Evidence for Both One- and Two-Electron Processes Napoline, J. Wesley; Krogman, Jeremy P.; Shi, Rena European Journal of Inorganic Chemistry, Vol. 2013, Issue 22-23 https://doi.org/10.1002/ejic.201300122	journal	May 2013
Synthesis and investigation of the metal–metal interactions in early/late heterobimetallic complexes linking group 5 imido fragments to Co(i) Evers, Deirdra A.; Bluestein, Alia H.; Foxman, Bruce M. Dalton Transactions, Vol. 41, Issue 26 https://doi.org/10.1039/c2dt00034b	journal	January 2012
Bimetallic Redox Synergy in Oxidative Palladium Catalysis Powers, David C.; Ritter, Tobias Accounts of Chemical Research, Vol. 45, Issue 6 https://doi.org/10.1021/ar2001974	journal	October 2011
Dinuclear phosphido- and arsenido-bridged early/late transition metal complexes. Efficient catalysts for ethylene polymerization Lindenberg, Frank; Shribman, Tal; Sieler, Joachim Journal of Organometallic Chemistry, Vol. 515, Issue 1-2 https://doi.org/10.1016/0022-328X(95)06060-A	journal	May 1996
Bimetallic catalysis by late transition metal complexes van den Beuken, Esther K.; Feringa, Ben L. Tetrahedron, Vol. 54, Issue 43 https://doi.org/10.1016/S0040-4020(98)00319-6	journal	October 1998
Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive Iwasaki, Takanori; Takagawa, Hiroaki; Singh, Surya P. Journal of the American Chemical Society, Vol. 135, Issue 26 https://doi.org/10.1021/ja404285b	journal	June 2013
Multimetallic Catalysis Based on Heterometallic Complexes and Clusters Buchwalter, Paulin; Rosé, Jacky; Braunstein, Pierre Chemical Reviews, Vol. 115, Issue 1 https://doi.org/10.1021/cr500208k	journal	November 2014
Formation of Heterobimetallic Zirconium/Cobalt Diimido Complexes via a Four-Electron Transformation Wu, Bing; Hernández Sánchez, Raúl; Bezpalko, Mark W. Inorganic Chemistry, Vol. 53, Issue 19 https://doi.org/10.1021/ic501490e	journal	September 2014
Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents Gonnard, Laurine; Guérinot, Amandine; Cossy, Janine Chemistry - A European Journal, Vol. 21, Issue 36 https://doi.org/10.1002/chem.201501543	journal	July 2015
Interaction and Activation of Carbon–Heteroatom π Bonds with a Zr/Co Heterobimetallic Complex Marquard, Seth L.; Bezpalko, Mark W.; Foxman, Bruce M. Organometallics, Vol. 33, Issue 8 https://doi.org/10.1021/om500217a	journal	April 2014
Mechanism and Catalytic Impact of Ir–Ta Heterobimetallic and Ir–P Transition Metal/Main Group Interactions on Alkene Hydrogenation Zhang, Ying; Roberts, Samuel P.; Bergman, Robert G. ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs501884j	journal	February 2015
Rate and equilibrium study of the reversible oxidative addition of silanes to the iridium center in Cp2Ta(.mu.-CH2)2Ir(CO)2 and of alkene hydrosilylation/isomerization catalyzed by this system Hostetler, Michael J.; Butts, Matthew D.; Bergman, Robert G. Organometallics, Vol. 12, Issue 1 https://doi.org/10.1021/om00025a015	journal	January 1993
A bimetallic hydroformylation catalyst: high regioselectivity through heterobimetallic cooperativity Rida, Maurice Abou; Smith, Anthony K. Journal of Molecular Catalysis A: Chemical, Vol. 202, Issue 1-2 https://doi.org/10.1016/S1381-1169(03)00234-6	journal	August 2003
A Bimetallic Nickel–Gallium Complex Catalyzes CO ₂ Hydrogenation via the Intermediacy of an Anionic d ¹⁰ Nickel Hydride Cammarota, Ryan C.; Vollmer, Matthew V.; Xie, Jing Journal of the American Chemical Society, Vol. 139, Issue 40 https://doi.org/10.1021/jacs.7b07911	journal	September 2017
Pd-, Ni-, Fe-, and Co-Catalyzed Cross-Couplings Using Functionalized Zn-, Mg-, Fe-, and In-Organometallics Knochel, Paul; Thaler, Tobias; Diene, Coura Israel Journal of Chemistry, Vol. 50, Issue 5-6 https://doi.org/10.1002/ijch.201000033	journal	November 2010
Base Metal Catalysts for Photochemical C–H Borylation That Utilize Metal–Metal Cooperativity Mazzacano, Thomas J.; Mankad, Neal P. Journal of the American Chemical Society, Vol. 135, Issue 46 https://doi.org/10.1021/ja408861p	journal	October 2013
Molecular Catalysts for Water Oxidation Blakemore, James D.; Crabtree, Robert H.; Brudvig, Gary W. Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00122	journal	July 2015
Metal–Metal Bonds in Catalysis Powers, Ian G.; Uyeda, Christopher ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b02692	journal	December 2016
Density Functionals with Broad Applicability in Chemistry Zhao, Yan; Truhlar, Donald G. Accounts of Chemical Research, Vol. 41, Issue 2 https://doi.org/10.1021/ar700111a	journal	February 2008

Cited By (2)

Dimerization of terminal alkynes promoted by a heterobimetallic Zr/Co complex Beattie, Jeffrey W.; Wang, Canning; Zhang, Hongtu Dalton Transactions, Vol. 49, Issue 8 https://doi.org/10.1039/d0dt00334d	journal	January 2020
Rare-earth/zinc heterometallic complexes containing both alkoxy-amino-bis(phenolato) and chiral salen ligands: synthesis and catalytic application for copolymerization of CO ₂ with cyclohexene oxide Xu, Ruoyu; Hua, Linyan; Li, Xiang Dalton Transactions, Vol. 48, Issue 28 https://doi.org/10.1039/c9dt00064j	journal	January 2019

Similar Records

Synthesis and reactivity of heterodinuclear iron, ruthenium, and cobalt compounds containing bridging dithiomethylene ligands. Attempted synthesis of the iron carbyne compound Cp(CO)Fe triple bond CSCH3

Thesis/Dissertation · 1984 · OSTI ID:6240423

Matachek, J R

Mild Catalytic methods for Alkyl-Alkyl Bond Formation

Other · 2009 · OSTI ID:962697

Vicic, David A

Pentamethylcyclopentadienyl aminoborollide derivatives of zirconium and hafnium. A new class of amphoteric molecule having both Lewis acidic and Lewis basic sites

Journal Article · 1994 · Journal of the American Chemical Society; (United States) · OSTI ID:7019670

Quan, R W; Bazan, G C; Kiely, A F; +2 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Why Two Metals Are Better Than One for Heterodinuclear Cobalt–Zirconium-Catalyzed Kumada Coupling

Citation Formats

References (85)

Cited By (2)

Similar Records

Related Subjects