Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration

Zhang, Guoqi; Wu, Jing; Zeng, Haisu; Neary, Michelle C.; Devany, Matthew; Zheng, Shengping; Dub, Pavel A.

doi:10.1021/acscatal.8b04096

Title: Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration

Journal Article · Mon Dec 31 00:00:00 UTC 2018 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.8b04096 · OSTI ID:1492666

^[1]; Wu, Jing ^[2]; Zeng, Haisu ^[2];

^[3]; Devany, Matthew ^[3]; Zheng, Shengping ^[3];

^[4]

City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College
City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College; City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Here, this paper reports the first example of dearomatization of ubiquitous terpyridine (tpy) ligands via 2'/6'-, 3'/5'-, or 4'-selective alkylation of the central pyridine ring. The reaction is mediated by the most abundant metal in the Earth’s crust, aluminum (Al), and depending on the conditions employed, exhibits ionic or radical character as suggested by experimental and computational analysis. In the latter case, intermediate formation of an AlIII complex supported by π-radical monoanionic ligand (tpy•)^1– is apparent. The 3'/5'-alkylation leads to unprecedented zwitterionic Meisenheimer Al^III complexes, which were identified as efficient precatalysts for the selective hydroboration of C=O and C≡C functionalities. Turnover numbers (TONs) up to ~1000 place the corresponding complexes in the category of the most efficient Al catalysts reported to date for the title reaction. The acquired data suggest that aluminum monohydrides, or more likely dihydrides, could be relevant catalytic species. Alternatively, one can also imagine a mechanistic scenario in which the dearomatized “chemically noninnocent” ligand acts as hydride donor, and a detailed investigation of this is warranted in the future.

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Research Organization:: Los Alamos National Laboratory (LANL)

Sponsoring Organization:: John Jay College; National Science Foundation (NSF); USDOE

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 1492666

Report Number(s):: LA-UR-18-24664

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Vol. 9; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (82)

Reaction of â[MnII(CH2tBu)2]â with Bidentate Diimine Ligands: From Simple Base Adducts to CbC Activation of the Ligand We are indebted to the CNRS and ESCPE Lyon for financial support. V.R. is grateful to the RÃ©gion RhÃ´ne-Alpes for a predoctoral fellowship. We also thank Prof. R. A. Andersen (U. C. Berkeley), Prof. Dr. Koelher (TUM), Dr. R. Gauvin (LCOMS), and Dr. C. Boisson (LCPP) for helpful discussions. Riollet, Virginie; CopÃ©ret, Christophe; Basset, Jean-Marie Angewandte Chemie International Edition, Vol. 41, Issue 16 https://doi.org/10.1002/1521-3773(20020816)41:16<3025::AID-ANIE3025>3.0.CO;2-B	journal	August 2002
An Aluminum Hydride That Functions like a Transition-Metal Catalyst Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli Angewandte Chemie International Edition, Vol. 54, Issue 35 https://doi.org/10.1002/anie.201503304	journal	June 2015
Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex Zhang, Guoqi; Zeng, Haisu; Wu, Jing Angewandte Chemie International Edition, Vol. 55, Issue 46 https://doi.org/10.1002/anie.201607579	journal	October 2016
Aluminum Hydride Catalyzed Hydroboration of Alkynes Bismuto, Alessandro; Thomas, Stephen P.; Cowley, Michael J. Angewandte Chemie International Edition, Vol. 55, Issue 49 https://doi.org/10.1002/anie.201609690	journal	November 2016
Interconversion of Molybdenum Imido and Amido Complexes by Proton-Coupled Electron Transfer Bezdek, Máté J.; Chirik, Paul J. Angewandte Chemie International Edition, Vol. 57, Issue 8 https://doi.org/10.1002/anie.201708406	journal	January 2018
Comparing Neutral (Monometallic) and Anionic (Bimetallic) Aluminum Complexes in Hydroboration Catalysis: Influences of Lithium Cooperation and Ligand Set Pollard, Victoria A.; Fuentes, M. Ángeles; Kennedy, Alan R. Angewandte Chemie International Edition, Vol. 57, Issue 33 https://doi.org/10.1002/anie.201806168	journal	August 2018
Straightforward Iron-Catalyzed Synthesis of Vinylboronates by the Hydroboration of Alkynes Haberberger, Michael; Enthaler, Stephan Chemistry - An Asian Journal, Vol. 8, Issue 1 https://doi.org/10.1002/asia.201200931	journal	November 2012
From Ruthenium to Iron and Manganese-A Mechanistic View on Challenges and Design Principles of Base-Metal Hydrogenation Catalysts Zell, Thomas; Langer, Robert ChemCatChem, Vol. 10, Issue 9 https://doi.org/10.1002/cctc.201701722	journal	March 2018
Catalysis by Aluminum(III) Complexes of Non-Innocent Ligands Berben, Louise A. Chemistry - A European Journal, Vol. 21, Issue 7 https://doi.org/10.1002/chem.201405400	journal	November 2014
Iron-Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation Espinal-Viguri, Maialen; Woof, Callum R.; Webster, Ruth L. Chemistry - A European Journal, Vol. 22, Issue 33 https://doi.org/10.1002/chem.201602818	journal	July 2016
Zinc Complexes with the Chelating Amido-Imino Ligand [1-n-Butyl-2-(2,6-diisopropylphenyl)iminoacenaphthen-1-yl]-2,6-diisopropylphenylamide (L): Synthesis, Molecular Structure and Reactivity of [(L)ZnCl]2, (L)Zn-nBu and (L)ZnN(SiMe3)2 Fedushkin, Igor L.; Tishkina, Alexandra N.; Fukin, Georgii K. European Journal of Inorganic Chemistry, Vol. 2008, Issue 3 https://doi.org/10.1002/ejic.200700796	journal	January 2008
Systematics and Future Projections Concerning Redox-Noninnocent Amide/Imine Ligands Caulton, Kenneth G. European Journal of Inorganic Chemistry, Vol. 2012, Issue 3 https://doi.org/10.1002/ejic.201100623	journal	November 2011
Radical Chemistry of Iminepyridine Ligands Budzelaar, Peter H. M. European Journal of Inorganic Chemistry, Vol. 2012, Issue 3 https://doi.org/10.1002/ejic.201100698	journal	September 2011
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
Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines King, Amanda E.; Stieber, S. Chantal E.; Henson, Neil J. European Journal of Inorganic Chemistry, Vol. 2016, Issue 11 https://doi.org/10.1002/ejic.201600143	journal	March 2016
Intrinsic reaction coordinate: Calculation, bifurcation, and automated search Maeda, Satoshi; Harabuchi, Yu; Ono, Yuriko International Journal of Quantum Chemistry, Vol. 115, Issue 5 https://doi.org/10.1002/qua.24757	journal	September 2014
Iron Group Hydrides in Noyori Bifunctional Catalysis Morris, Robert H. The Chemical Record, Vol. 16, Issue 6 https://doi.org/10.1002/tcr.201600080	journal	August 2016
Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane: Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane Franz, Daniel; Sirtl, Lorenz; Pöthig, Alexander Zeitschrift für anorganische und allgemeine Chemie, Vol. 642, Issue 22 https://doi.org/10.1002/zaac.201600313	journal	November 2016
Stable 1,4-diaza-1,3-butadiene(α-diimine)-zinc and -aluminium radicals formed in single electron transfer reactions: their consequences for organic syntheses Van Koten, Gerard; Jastrzebski, Johann T. B. H.; Vrieze, Kees Journal of Organometallic Chemistry, Vol. 250, Issue 1 https://doi.org/10.1016/0022-328X(83)85039-6	journal	July 1983
The synthesis of 2,2′:6′,2″-terpyridine ligands — versatile building blocks for supramolecular chemistry Cargill Thompson, Alexander M. W. Coordination Chemistry Reviews, Vol. 160 https://doi.org/10.1016/S0010-8545(96)01283-0	journal	April 1997
Synthesis and structural characterisation of aluminium imino-amide and pyridyl-amide complexes: bulky monoanionic N,N chelate ligands via methyl group transfer1Dedicated to Professor Ken Wade on the occasion of his 65th birthday in recognition of his outstanding contributions to inorganic chemistry.1 Gibson, Vernon C.; Redshaw, Carl; White, Andrew J. P. Journal of Organometallic Chemistry, Vol. 550, Issue 1-2 https://doi.org/10.1016/S0022-328X(97)00552-4	journal	January 1998
Soluble aluminum hydrides function as catalysts in deprotonation, insertion, and activation reactions Li, Wenling; Ma, Xiaoli; Walawalkar, Mrinalini G. Coordination Chemistry Reviews, Vol. 350 https://doi.org/10.1016/j.ccr.2017.03.017	journal	November 2017
Reaction: Earth-Abundant Metal Catalysts for Energy Conversions Bullock, R. Morris Chem, Vol. 2, Issue 4 https://doi.org/10.1016/j.chempr.2017.03.019	journal	April 2017
(Amidomethyl)pyridine zirconium and hafnium complexes: Synthesis and structural characterization Nienkemper, Katrin; Kehr, Gerald; Kehr, Seda Journal of Organometallic Chemistry, Vol. 693, Issue 8-9 https://doi.org/10.1016/j.jorganchem.2007.12.004	journal	April 2008
(CAAC)CuX-catalyzed hydroboration of terminal alkynes with pinacolborane directed by the X-ligand Romero, Erik A.; Jazzar, Rodolphe; Bertrand, Guy Journal of Organometallic Chemistry, Vol. 829 https://doi.org/10.1016/j.jorganchem.2016.09.025	journal	February 2017
Recent developments in alkyne borylations Barbeyron, Renaud; Benedetti, Erica; Cossy, Janine Tetrahedron, Vol. 70, Issue 45 https://doi.org/10.1016/j.tet.2014.06.026	journal	November 2014
Getting Down to Earth: The Renaissance of Catalysis with Abundant Metals Chirik, Paul; Morris, Robert Accounts of Chemical Research, Vol. 48, Issue 9 https://doi.org/10.1021/acs.accounts.5b00385	journal	August 2015
Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis Zweig, Joshua E.; Kim, Daria E.; Newhouse, Timothy R. Chemical Reviews, Vol. 117, Issue 18 https://doi.org/10.1021/acs.chemrev.6b00833	journal	May 2017
Mechanism of Alkyl Migration in Diorganomagnesium 2,6-Bis(imino)pyridine Complexes: Formation of Grignard-Type Complexes with Square-Planar Mg(II) Centers Sandoval, John J.; Palma, Pilar; Álvarez, Eleuterio Organometallics, Vol. 35, Issue 18 https://doi.org/10.1021/acs.organomet.6b00528	journal	September 2016
Neutral Bis(imino)-1,4-dihydropyridinate and Cationic Bis(imino)pyridine σ-Alkylzinc(II) Complexes as Hydride Exchange Systems: Classic Organometallic Chemistry Meets Ligand-Centered, Biomimetic Reactivity Sandoval, John J.; Álvarez, Eleuterio; Palma, Pilar Organometallics, Vol. 37, Issue 11 https://doi.org/10.1021/acs.organomet.8b00183	journal	May 2018
A Pharmaceutical Industry Perspective on Sustainable Metal Catalysis Hayler, John D.; Leahy, David K.; Simmons, Eric M. Organometallics, Vol. 38, Issue 1 https://doi.org/10.1021/acs.organomet.8b00566	journal	October 2018
Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds Jakhar, Vineet Kumar; Barman, Milan Kr.; Nembenna, Sharanappa Organic Letters, Vol. 18, Issue 18 https://doi.org/10.1021/acs.orglett.6b02310	journal	August 2016
Hydroboration of Alkynes Catalyzed by Pyrrolide-Based PNP Pincer–Iron Complexes Nakajima, Kazunari; Kato, Takeru; Nishibayashi, Yoshiaki Organic Letters, Vol. 19, Issue 16 https://doi.org/10.1021/acs.orglett.7b01995	journal	July 2017
Catalytic Hydroboration of Carbonyl Derivatives, Imines, and Carbon Dioxide Chong, Che Chang; Kinjo, Rei ACS Catalysis, Vol. 5, Issue 6 https://doi.org/10.1021/acscatal.5b00428	journal	April 2015
Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst Weidner, Victoria L.; Barger, Christopher J.; Delferro, Massimiliano ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b03332	journal	January 2017
Metal–Ligand Bifunctional Catalysis: The “Accepted” Mechanism, the Issue of Concertedness, and the Function of the Ligand in Catalytic Cycles Involving Hydrogen Atoms Dub, Pavel A.; Gordon, John C. ACS Catalysis, Vol. 7, Issue 10 https://doi.org/10.1021/acscatal.7b01791	journal	September 2017
New Tricks for an Old Dog: Aluminum Compounds as Catalysts in Reduction Chemistry Nikonov, Georgii I. ACS Catalysis, Vol. 7, Issue 10 https://doi.org/10.1021/acscatal.7b02460	journal	September 2017
Aluminum-Catalyzed Hydroboration of Alkenes Bismuto, Alessandro; Cowley, Michael J.; Thomas, Stephen P. ACS Catalysis, Vol. 8, Issue 3 https://doi.org/10.1021/acscatal.7b04279	journal	January 2018
Some aspects of anionic .sigma.-complexes Artamkina, G. A.; Egorov, M. P.; Beletskaya, I. P. Chemical Reviews, Vol. 82, Issue 4 https://doi.org/10.1021/cr00050a004	journal	August 1982
Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions Lyaskovskyy, Volodymyr; de Bruin, Bas ACS Catalysis, Vol. 2, Issue 2 https://doi.org/10.1021/cs200660v	journal	January 2012
“Turning Over” Definitions in Catalytic Cycles Kozuch, Sebastian; Martin, Jan M. L. ACS Catalysis, Vol. 2, Issue 12 https://doi.org/10.1021/cs3005264	journal	November 2012
High-Activity Cobalt Catalysts for Alkene Hydroboration with Electronically Responsive Terpyridine and α-Diimine Ligands Palmer, W. Neil; Diao, Tianning; Pappas, Iraklis ACS Catalysis, Vol. 5, Issue 2 https://doi.org/10.1021/cs501639r	journal	December 2014
Performance of Density Functional Theory for Second Row (4 d ) Transition Metal Thermochemistry Laury, Marie L.; Wilson, Angela K. Journal of Chemical Theory and Computation, Vol. 9, Issue 9 https://doi.org/10.1021/ct400379z	journal	August 2013
The Renaissance of Aluminum Chemistry ^† Roesky, Herbert W. Inorganic Chemistry, Vol. 43, Issue 23 https://doi.org/10.1021/ic0400641	journal	November 2004
Preface: Forum on Redox-Active Ligands Chirik, Paul J. Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic201881k	journal	October 2011
Evidence for a Ni ^I Active Species in the Catalytic Cross-Coupling of Alkyl Electrophiles Anderson, Thomas J.; Jones, Gavin D.; Vicic, David A. Journal of the American Chemical Society, Vol. 126, Issue 26 https://doi.org/10.1021/ja0483903	journal	July 2004
Dearomatization and Functionalization of Terpyridine by Lutetium(III) Alkyl Complexes Jantunen, Kimberly C.; Scott, Brian L.; Hay, P. Jeffrey Journal of the American Chemical Society, Vol. 128, Issue 19 https://doi.org/10.1021/ja061161r	journal	April 2006
Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling Catalyst Jones, Gavin D.; Martin, Jason L.; McFarland, Chris Journal of the American Chemical Society, Vol. 128, Issue 40 https://doi.org/10.1021/ja063334i	journal	October 2006
A Powerful Aluminum Catalyst for the Synthesis of Highly Functional Organic Carbonates Whiteoak, Christopher J.; Kielland, Nicola; Laserna, Victor Journal of the American Chemical Society, Vol. 135, Issue 4 https://doi.org/10.1021/ja311053h	journal	January 2013
Aluminum–Ligand Cooperative N–H Bond Activation and an Example of Dehydrogenative Coupling Myers, Thomas W.; Berben, Louise A. Journal of the American Chemical Society, Vol. 135, Issue 27 https://doi.org/10.1021/ja4032874	journal	June 2013
Low Coordinate Germanium(II) and Tin(II) Hydride Complexes: Efficient Catalysts for the Hydroboration of Carbonyl Compounds Hadlington, Terrance J.; Hermann, Markus; Frenking, Gernot Journal of the American Chemical Society, Vol. 136, Issue 8 https://doi.org/10.1021/ja5006477	journal	February 2014
Life and Death of an Active Ethylene Polymerization Catalyst. Ligand Involvement in Catalyst Activation and Deactivation. Isolation and Characterization of Two Unprecedented Neutral and Anionic Vanadium(I) Alkyls Reardon, Damien; Conan, Françoise; Gambarotta, Sandro Journal of the American Chemical Society, Vol. 121, Issue 40 https://doi.org/10.1021/ja990263x	journal	October 1999
An Aluminum Dihydride Working as a Catalyst in Hydroboration and Dehydrocoupling Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.6b00032	journal	February 2016
Alkali Metal Hydridotriphenylborates [(L)M][HBPh ₃ ] (M = Li, Na, K): Chemoselective Catalysts for Carbonyl and CO ₂ Hydroboration Mukherjee, Debabrata; Osseili, Hassan; Spaniol, Thomas P. Journal of the American Chemical Society, Vol. 138, Issue 34 https://doi.org/10.1021/jacs.6b06319	journal	August 2016
Alkylation Reactions of Dialkylzinc Compounds with 1,4-Diaza-1,3-butadienes: Cationic and Radical Anionic Organozinc Intermediates. Molecular Structure of the Cationic Organozinc Species [MeZn(tert-BuN:CHCH:N-tert-Bu)]O3SCF3 and Me2Zn(bpy) (bpy = 2,2'-Bipyridine) Wissing, Elmo; Kaupp, Martin; Boersma, Jaap Organometallics, Vol. 13, Issue 6 https://doi.org/10.1021/om00018a029	journal	June 1994
Organozinc .alpha.-Diimine Radicals, Synthesis and Reactivity toward Alkyl Halides Wissing, Elmo; van der Linden, Steven; Rijnberg, Evelien Organometallics, Vol. 13, Issue 7 https://doi.org/10.1021/om00019a017	journal	July 1994
Reaction of the Diimine Pyridine Ligand with Aluminum Alkyls: An Unexpectedly Complex Reaction Knijnenburg, Quinten; Smits, Jan M. M.; Budzelaar, Peter H. M. Organometallics, Vol. 25, Issue 4 https://doi.org/10.1021/om050936m	journal	February 2006
Selective Alkylation of 2,6-Diiminopyridine Ligands by Dialkylmanganese Reagents: A “One-Pot” Synthetic Methodology Cámpora, Juan; Pérez, Carmen M.; Rodríguez-Delgado, Antonio Organometallics, Vol. 26, Issue 4 https://doi.org/10.1021/om0609517	journal	February 2007
σ-Bond Metathesis: A 30-Year Retrospective Waterman, Rory Organometallics, Vol. 32, Issue 24 https://doi.org/10.1021/om400760k	journal	September 2013
Activation and discovery of earth-abundant metal catalysts using sodium tert-butoxide Docherty, Jamie H.; Peng, Jingying; Dominey, Andrew P. Nature Chemistry, Vol. 9, Issue 6 https://doi.org/10.1038/nchem.2697	journal	January 2017
The role of the metal-bound N–H functionality in Noyori-type molecular catalysts Dub, Pavel A.; Gordon, John C. Nature Reviews Chemistry, Vol. 2, Issue 12 https://doi.org/10.1038/s41570-018-0049-z	journal	November 2018
Outer sphere hydrogenation catalysis Eisenstein, Odile; Crabtree, Robert H. New J. Chem., Vol. 37, Issue 1 https://doi.org/10.1039/C2NJ40659D	journal	January 2013
Selection of boron reagents for Suzuki–Miyaura coupling Lennox, Alastair J. J.; Lloyd-Jones, Guy C. Chem. Soc. Rev., Vol. 43, Issue 1 https://doi.org/10.1039/C3CS60197H	journal	January 2014
Non-innocent ligands Berben, Louise A.; de Bruin, Bas; Heyduk, Alan F. Chemical Communications, Vol. 51, Issue 9 https://doi.org/10.1039/C4CC90480J	journal	January 2015
Extremely efficient hydroboration of ketones and aldehydes by copper carbene catalysis Bagherzadeh, Sharareh; Mankad, Neal P. Chemical Communications, Vol. 52, Issue 19 https://doi.org/10.1039/C5CC09162D	journal	January 2016
Magnesium hydridotriphenylborate [Mg(thf) ₆ ][HBPh ₃ ] ₂ : a versatile hydroboration catalyst Mukherjee, Debabrata; Shirase, Satoru; Spaniol, Thomas P. Chemical Communications, Vol. 52, Issue 89 https://doi.org/10.1039/C6CC06805G	journal	January 2016
The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts Dub, Pavel A.; Gordon, John C. Dalton Transactions, Vol. 45, Issue 16 https://doi.org/10.1039/C6DT00476H	journal	January 2016
Hydroboration of alkynes and nitriles using an α-diimine cobalt hydride catalyst Ben-Daat, Hagit; Rock, Christopher L.; Flores, Marco Chemical Communications, Vol. 53, Issue 53 https://doi.org/10.1039/C7CC02281F	journal	January 2017
Lithium diamidodihydridoaluminates: bimetallic cooperativity in catalytic hydroboration and metallation applications Pollard, Victoria A.; Orr, Samantha A.; McLellan, Ross Chemical Communications, Vol. 54, Issue 10 https://doi.org/10.1039/C7CC08214B	journal	January 2018
Catalytic (de)hydrogenation promoted by non-precious metals – Co, Fe and Mn: recent advances in an emerging field Filonenko, Georgy A.; van Putten, Robbert; Hensen, Emiel J. M. Chemical Society Reviews, Vol. 47, Issue 4 https://doi.org/10.1039/C7CS00334J	journal	January 2018
Catalytic hydroboration of aldehydes, ketones, alkynes and alkenes initiated by NaOH Wu, Yile; Shan, Changkai; Ying, Jianxi Green Chemistry, Vol. 19, Issue 17 https://doi.org/10.1039/C7GC01632H	journal	January 2017
Complexation of dimethylmagnesium with α-diimines; structural and EPR characterisation of single electron and alkyl transfer products Bailey, Philip J.; Dick, Caroline M.; Fabre, Sylvie Dalton Transactions, Issue 13 https://doi.org/10.1039/b514591k	journal	January 2006
Ligand-centred reactivity in diiminepyridine complexes Knijnenburg, Quinten; Gambarotta, Sandro; Budzelaar, Peter H. M. Dalton Transactions, Issue 46 https://doi.org/10.1039/b612251e	journal	January 2006
Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin Trost, Barry M.; Ball, Zachary T. Synthesis, Vol. 2005, Issue 06 https://doi.org/10.1055/s-2005-861874	journal	January 2005
Metal complexes with non-innocent ligands Butin, Kim P.; Beloglazkina, Elena K.; Zyk, Nikolai V. Russian Chemical Reviews, Vol. 74, Issue 6 https://doi.org/10.1070/RC2005v074n06ABEH000977	journal	June 2005
Radical Ligands Confer Nobility on Base-Metal Catalysts Chirik, P. J.; Wieghardt, K. Science, Vol. 327, Issue 5967 https://doi.org/10.1126/science.1183281	journal	February 2010
Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines Jagadeesh, R. V.; Surkus, A. -E.; Junge, H. Science, Vol. 342, Issue 6162 https://doi.org/10.1126/science.1242005	journal	November 2013
Cobalt Precursors for High-Throughput Discovery of Base Metal Asymmetric Alkene Hydrogenation Catalysts Friedfeld, M. R.; Shevlin, M.; Hoyt, J. M. Science, Vol. 342, Issue 6162 https://doi.org/10.1126/science.1243550	journal	November 2013
Amine(imine)diphosphine Iron Catalysts for Asymmetric Transfer Hydrogenation of Ketones and Imines Zuo, W.; Lough, A. J.; Li, Y. F. Science, Vol. 342, Issue 6162 https://doi.org/10.1126/science.1244466	journal	November 2013
Abundant Metals Give Precious Hydrogenation Performance Bullock, R. M. Science, Vol. 342, Issue 6162 https://doi.org/10.1126/science.1247240	journal	November 2013
Hydrogenation of carboxylic acids with a homogeneous cobalt catalyst Korstanje, T. J.; Ivar van der Vlugt, J.; Elsevier, C. J. Science, Vol. 350, Issue 6258 https://doi.org/10.1126/science.aaa8938	journal	October 2015
Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction Friedfeld, Max R.; Zhong, Hongyu; Ruck, Rebecca T. Science, Vol. 360, Issue 6391 https://doi.org/10.1126/science.aar6117	journal	May 2018

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Program Document · Sun Jan 01 04:00:00 UTC 2006 · OSTI ID:1218590

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Inorganic and Physical Chemistry
Organic Chemistry

CCDC 1585884: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1q77kr The current record is supplemented by this dataset	dataset	January 2019
CCDC 1585885: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1q77ls The current record is supplemented by this dataset	dataset	January 2019
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