Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration

Eedugurala, Naresh; Wang, Zhuoran; Chaudhary, Umesh; Nelson, Nicholas; Kandel, Kapil; Kobayashi, Takeshi; Slowing, Igor I.; Pruski, Marek; Sadow, Aaron D.

doi:10.1021/acscatal.5b01671

Title: Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration

Journal Article · Tue Nov 03 23:00:00 EST 2015 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.5b01671 · OSTI ID:1226905

Eedugurala, Naresh ^[1]; Wang, Zhuoran ^[1]; Chaudhary, Umesh ^[1]; Nelson, Nicholas ^[1]; Kandel, Kapil ^[1]; Kobayashi, Takeshi ^[1]; Slowing, Igor I. ^[1]; Pruski, Marek ^[1]; Sadow, Aaron D. ^[1]

Iowa State Univ., Ames, IA (United States)

The hydroboration of aldehydes and ketones using a silica-supported zirconium catalyst is reported. Reaction of Zr(NMe₂)₄ and mesoporous silica nanoparticles (MSN) provides the catalytic material Zr(NMe₂)_n@MSN. Exhaustive characterization of Zr(NMe₂)_n@MSN with solid-state (SS)NMR and infrared spectroscopy, as well as through reactivity studies, suggests its surface structure is primarily ≡SiOZr(NMe₂)₃. The presence of these nitrogen-containing zirconium sites is supported by ¹⁵N NMR spectroscopy, including natural abundance ¹⁵N NMR measurements using dynamic nuclear polarization (DNP) SSNMR. The Zr(NMe₂)_n@MSN material reacts with pinacolborane (HBpin) to provide Me₂NBpin and the material ZrH/Bpin@MSN that is composed of interacting surface-bonded zirconium hydride and surface-bonded borane ≡SiOBpin moieties in an approximately 1:1 ratio, as well as zirconium sites coordinated by dimethylamine. The ZrH/Bpin@MSN is characterized by ¹H/²H and ¹¹B SSNMR and infrared spectroscopy and through its reactivity with D₂. The zirconium hydride material or the zirconium amide precursor Zr(NMe₂)_n@MSN catalyzes the selective hydroboration of aldehydes and ketones with HBpin in the presence of functional groups that are often reduced under hydroboration conditions or are sensitive to metal hydrides, including olefins, alkynes, nitro groups, halides, and ethers. Remarkably, this catalytic material may be recycled without loss of activity at least eight times, and air-exposed materials are catalytically active. These supported zirconium centers are robust catalytic sites for carbonyl reduction and that surface-supported, catalytically reactive zirconium hydride may be generated from zirconium-amide or zirconium alkoxide sites.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1226905

Report Number(s):: IS--J--8514

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 5 Vol. 2015; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (60)

Surface Organometallic Chemistry on Oxides: Selective Catalytic Low-Temperature Hydrogenolysis of Alkanes by a Highly Electrophilic Zirconium Hydride Complex Supported on Silica Lecuyer, Christine; Quignard, Francoise; Choplin, Agnès Angewandte Chemie International Edition in English, Vol. 30, Issue 12 https://doi.org/10.1002/anie.199116601	journal	December 1991
New Ligands for the Titanium(IV)-Induced Asymmetric Reduction of Ketones with Catecholborane Almqvist, Fredrik; Torstensson, Lillemor; Gudmundsson, Anette Angewandte Chemie International Edition in English, Vol. 36, Issue 4 https://doi.org/10.1002/anie.199703761	journal	March 1997
Homogeneous and Heterogeneous Catalysis: Bridging the Gap through Surface Organometallic Chemistry Copéret, Christophe; Chabanas, Mathieu; Petroff Saint-Arroman, Romain Angewandte Chemie International Edition, Vol. 42, Issue 2, p. 156-181 https://doi.org/10.1002/anie.200390072	journal	January 2003
Alkoxide Activation of Aminoboranes towards Selective Amination Solé, Cristina; Fernández, Elena Angewandte Chemie International Edition, Vol. 52, Issue 43 https://doi.org/10.1002/anie.201305098	journal	September 2013
Well-Defined Single-Site Monohydride Silica-Supported Zirconium from Azazirconacyclopropane Hamzaoui, Bilel; Eter, Mohamad El; Abou-hamad, Edy Chemistry - A European Journal, Vol. 21, Issue 11 https://doi.org/10.1002/chem.201405788	journal	January 2015
Probing Quadrupolar Nuclei by Solid-State NMR Spectroscopy: Recent Advances Fernandez, Christian; Pruski, Marek Solid State NMR: Topics in Current Chemistry https://doi.org/10.1007/128_2011_141	book	January 2011
Formation of zirconium hydrides in supported organozirconium catalysts and their role in ethylene polymerization Zakharov, V. A.; Dudchenko, V. K.; Paukshtis, E. A. Journal of Molecular Catalysis, Vol. 2, Issue 6 https://doi.org/10.1016/0304-5102(77)80013-8	journal	September 1977
Hydride complexes of titanium and zirconium attached to SiO2 as hydrogenation catalysts Yermakovt, Y. I.; Ryndin, Y. A.; Alekseev, O. S. Journal of Molecular Catalysis, Vol. 49, Issue 2 https://doi.org/10.1016/0304-5102(89)80044-6	journal	January 1989
Surface organometallic chemistry of zirconium: Application to the stoichiometric activation of the CH bonds of alkanes and to the low-temperature catalytic hydrogenolysis of alkanes Quignard, Françoise; Le´cuyer, Christine; Choplin, Agne`s Journal of Molecular Catalysis, Vol. 74, Issue 1-3 https://doi.org/10.1016/0304-5102(92)80253-D	journal	July 1992
Tris(trimethylsilyl)silyllithium · 3 THF: a stable crystalline silyllithium reagent Gutekunst, Gerhard; G. Brook, Adrian Journal of Organometallic Chemistry, Vol. 225, Issue 1 https://doi.org/10.1016/S0022-328X(00)86805-9	journal	February 1982
Tetrakis(trimethylsilyl)silane Gilman, Henry; Smith, Clifford L. Journal of Organometallic Chemistry, Vol. 8, Issue 2 https://doi.org/10.1016/S0022-328X(00)91037-4	journal	May 1967
Tetrakisdimethylamidozirconium and its dimethylamido lithium adduct: Structures of [zr(nme2)4]2 and zr(nme2)6li2(thf)2 Chisholm, Malcolm H.; Hammond, Charles E.; Huffman, John C. Polyhedron, Vol. 7, Issue 24 https://doi.org/10.1016/S0277-5387(00)83867-X	journal	January 1988
Indirectly detected heteronuclear correlation solid-state NMR spectroscopy of naturally abundant 15N nuclei Althaus, Stacey M.; Mao, Kanmi; Stringer, John A. Solid State Nuclear Magnetic Resonance, Vol. 57-58 https://doi.org/10.1016/j.ssnmr.2013.11.001	journal	February 2014
The coordination polymerization of silanes to polysilanes by a ".sigma.-bond metathesis" mechanism. Implications for linear chain growth Tilley, T. Don Accounts of Chemical Research, Vol. 26, Issue 1 https://doi.org/10.1021/ar00025a004	journal	January 1993
Metathesis of Alkanes and Related Reactions Basset, Jean-Marie; Coperet, Christophe; Soulivong, Daravong Accounts of Chemical Research, Vol. 43, Issue 2, p. 323-334 https://doi.org/10.1021/ar900203a	journal	February 2010
Bifunctional Adsorbent-Catalytic Nanoparticles for the Refining of Renewable Feedstocks Kandel, Kapil; Frederickson, Conerd; Smith, Erica A. ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs4008039	journal	November 2013
Surface organometallic chemistry: synthesis and characterization of a tris(neopentyl)zirconium(IV) complex grafted to the surface of a partially dehydroxylated silica Quignard, Francoise; Lecuyer, Christine; Bougault, Catherine Inorganic Chemistry, Vol. 31, Issue 5 https://doi.org/10.1021/ic00031a042	journal	March 1992
Zirconium-catalyzed highly regioselective hydrosilation reaction of alkenes and x-ray structures of silyl(hydrido)zirconocene derivatives Takahashi, Tamotsu; Hasegawa, Maki; Suzuki, Noriyuki Journal of the American Chemical Society, Vol. 113, Issue 22 https://doi.org/10.1021/ja00022a077	journal	October 1991
Organolanthanide-catalyzed hydroboration of olefins Harrison, Karl N.; Marks, Tobin J. Journal of the American Chemical Society, Vol. 114, Issue 23 https://doi.org/10.1021/ja00049a083	journal	November 1992
Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations Willoughby, Christopher A.; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 116, Issue 20 https://doi.org/10.1021/ja00099a012	journal	October 1994
Enantioselective Hydrosilylation of Ketones with a Chiral Titanocene Catalyst Carter, Mary Beth; Schiott, Birgit; Gutierrez, Alberto Journal of the American Chemical Society, Vol. 116, Issue 26 https://doi.org/10.1021/ja00105a006	journal	December 1994
Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Kinetic and Mechanistic Investigations Willoughby, Christopher A.; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 116, Issue 26 https://doi.org/10.1021/ja00105a011	journal	December 1994
Regioselection and Enantioselection in Organolanthanide-Catalyzed Olefin Hydrosilylation. A Kinetic and Mechanistic Study Fu, Peng-Fei; Brard, Laurent; Li, Yanwu Journal of the American Chemical Society, Vol. 117, Issue 27 https://doi.org/10.1021/ja00132a015	journal	July 1995
Multiple-Quantum Magic-Angle Spinning NMR: A New Method for the Study of Quadrupolar Nuclei in Solids Medek, Ales; Harwood, John S.; Frydman, Lucio Journal of the American Chemical Society, Vol. 117, Issue 51 https://doi.org/10.1021/ja00156a015	journal	December 1995
Highly reactive organolanthanides. A mechanistic study of catalytic olefin hydrogenation by bis(pentamethylcyclopentadienyl) and related 4f complexes Jeske, Gerald; Lauke, Harald; Mauermann, Heiko Journal of the American Chemical Society, Vol. 107, Issue 26 https://doi.org/10.1021/ja00312a052	journal	December 1985
Reactions of water and ammonia with bis(pentamethylcyclopentadienyl) complexes of zirconium and hafnium Hillhouse, Gregory L.; Bercaw, John E. Journal of the American Chemical Society, Vol. 106, Issue 19 https://doi.org/10.1021/ja00331a015	journal	September 1984
Stoichiometric hydrogen reduction of carbon monoxide to methanol promoted by derivatives of bis(pentamethylcyclopentadienyl)zirconium Manriquez, Juan M.; McAlister, Donald R.; Sanner, Robert D. Journal of the American Chemical Society, Vol. 98, Issue 21 https://doi.org/10.1021/ja00437a069	journal	October 1976
An Efficient, Single-Source Molecular Precursor to Silicoaluminophosphates Fujdala, Kyle L.; Tilley, T. Don Journal of the American Chemical Society, Vol. 123, Issue 41 https://doi.org/10.1021/ja0167295	journal	October 2001
Molecular Understanding of the Formation of Surface Zirconium Hydrides upon Thermal Treatment under Hydrogen of [(⋮SiO)Zr(CH ₂ t Bu) ₃ ] by Using Advanced Solid-State NMR Techniques Rataboul, Franck; Baudouin, Anne; Thieuleux, Chloé Journal of the American Chemical Society, Vol. 126, Issue 39 https://doi.org/10.1021/ja038486h	journal	October 2004
Surface Enhanced NMR Spectroscopy by Dynamic Nuclear Polarization Lesage, Anne; Lelli, Moreno; Gajan, David Journal of the American Chemical Society, Vol. 132, Issue 44 https://doi.org/10.1021/ja104771z	journal	November 2010
Large Molecular Weight Nitroxide Biradicals Providing Efficient Dynamic Nuclear Polarization at Temperatures up to 200 K Zagdoun, Alexandre; Casano, Gilles; Ouari, Olivier Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja405813t	journal	August 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
Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes Wu, Jessica Y.; Moreau, Benoît; Ritter, Tobias Journal of the American Chemical Society, Vol. 131, Issue 36 https://doi.org/10.1021/ja9048493	journal	August 2009
Efficient Synthesis of Chiral ansa -Metallocenes by Amine Elimination. Synthesis, Structure, and Reactivity of rac -(EBI)Zr(NMe ₂ ) ₂ Diamond, Gary M.; Jordan, Richard F.; Petersen, Jeffrey L. Journal of the American Chemical Society, Vol. 118, Issue 34 https://doi.org/10.1021/ja9604830	journal	January 1996
Highly Enantioselective Imine Hydrosilylation Using ( S,S )-Ethylenebis(η ⁵ -tetrahydroindenyl)titanium Difluoride Verdaguer, Xavier; Lange, Udo E. W.; Reding, Matthew T. Journal of the American Chemical Society, Vol. 118, Issue 28 https://doi.org/10.1021/ja960808c	journal	January 1996
Titanocene-Catalyzed Asymmetric Ketone Hydrosilylation: The Effect of Catalyst Activation Protocol and Additives on the Reaction Rate and Enantioselectivity Yun, Jaesook; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 121, Issue 24 https://doi.org/10.1021/ja990450v	journal	June 1999
Selective hydrosilylation of alkenes catalyzed by an organoyttrium complex Molander, Gary A.; Julius, Manfred The Journal of Organic Chemistry, Vol. 57, Issue 23 https://doi.org/10.1021/jo00049a056	journal	November 1992
Conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds by catecholborane Evans, David A.; Fu, Gregory C. The Journal of Organic Chemistry, Vol. 55, Issue 22 https://doi.org/10.1021/jo00309a007	journal	October 1990
Hydroboration of Alkynes with Pinacolborane Catalyzed by HZrCp2Cl Pereira, Schubert; Srebnik, Morris Organometallics, Vol. 14, Issue 7 https://doi.org/10.1021/om00007a003	journal	July 1995
Selective Hydrosilylation of Alkynes Catalyzed by an Organoyttrium Complex Molander, Gary A.; Retsch, William H. Organometallics, Vol. 14, Issue 10 https://doi.org/10.1021/om00010a022	journal	October 1995
Hydrogen/Deuterium Exchange Kinetics by a Silica-Supported Zirconium Hydride Catalyst: Evidence for a σ-Bond Metathesis Mechanism Casty, Gary L.; Matturro, Michael G.; Myers, Gary R. Organometallics, Vol. 20, Issue 11 https://doi.org/10.1021/om0007926	journal	May 2001
Spontaneous Evolution of Silica-Supported Ti Amide Fragments to Imine and Imido Complexes Beaudoin, Marcel; Scott, Susannah L. Organometallics, Vol. 20, Issue 2 https://doi.org/10.1021/om000915m	journal	January 2001
Synthesis of Ruthenium Boryl Analogues of the Shvo Metal−Ligand Bifunctional Catalyst Koren-Selfridge, Liza; Query, Ian P.; Hanson, Joel A. Organometallics, Vol. 29, Issue 17 https://doi.org/10.1021/om1005808	journal	August 2010
Magnesium-Catalyzed Hydroboration of Pyridines Arrowsmith, Merle; Hill, Michael S.; Hadlington, Terrance Organometallics, Vol. 30, Issue 21 https://doi.org/10.1021/om2008138	journal	November 2011
Titanocene(II)-Catalyzed Hydroboration of Carbonyl Compounds Oluyadi, Abdulafeez A.; Ma, Shuhua; Muhoro, Clare N. Organometallics, Vol. 32, Issue 1 https://doi.org/10.1021/om300828m	journal	December 2012
σ-Bond Metathesis: A 30-Year Retrospective Waterman, Rory Organometallics, Vol. 32, Issue 24 https://doi.org/10.1021/om400760k	journal	September 2013
C–H and C–C Activation of n -Butane with Zirconium Hydrides Supported on SBA15 Containing N-Donor Ligands: [(≡SiNH−)(≡SiX−)ZrH ₂ ], [(≡SiNH−)(≡SiX−) ₂ ZrH], and[(≡SiN═)(≡SiX−)ZrH] (X = −NH–, −O−). A DFT Study Pasha, Farhan Ahmad; Bendjeriou-Sedjerari, Anissa; Huang, Kuo-Wei Organometallics, Vol. 33, Issue 13 https://doi.org/10.1021/om5000858	journal	July 2014
Hydrosilylation Catalysis by C ₂ -Symmetric Bis(silylamido) Complexes of Yttrium Gountchev, Tomislav I.; Tilley, T. Don Organometallics, Vol. 18, Issue 26 https://doi.org/10.1021/om990690j	journal	December 1999
A zwitterionic zirconium complex that catalyzes hydroamination of aminoalkenes at room temperature Manna, Kuntal; Ellern, Arkady; Sadow, Aaron D. Chem. Commun., Vol. 46, Issue 2 https://doi.org/10.1039/B918989K	journal	January 2010
Catalytic hydroboration by an imido-hydrido complex of Mo( iv ) Khalimon, Andrey Y.; Farha, Philip; Kuzmina, Lyudmila G. Chem. Commun., Vol. 48, Issue 3 https://doi.org/10.1039/C1CC14508H	journal	January 2012
Magnesium-catalyzed hydroboration of esters: evidence for a new zwitterionic mechanism Mukherjee, Debabrata; Ellern, Arkady; Sadow, Aaron D. Chem. Sci., Vol. 5, Issue 3 https://doi.org/10.1039/C3SC52793J	journal	January 2014
Methane activation by silica-supported Zr( iv ) hydrides: the dihydride [(SiO) ₂ ZrH ₂ ] is much faster than the monohydride [(SiO) ₃ ZrH] Thieuleux, Chloé; Quadrelli, Elsje Alessandra; Basset, Jean-Marie Chem. Commun., Issue 15 https://doi.org/10.1039/b404749d	journal	January 2004
Magnesium-catalysed hydroboration of aldehydes and ketones Arrowsmith, Merle; Hadlington, Terrance J.; Hill, Michael S. Chemical Communications, Vol. 48, Issue 38 https://doi.org/10.1039/c2cc30565h	journal	January 2012
Alkane activation by a highly electrophilic zirconium hydride complex supported on silica Quignard, Francoise; Choplin, Agn�s; Basset, Jean-Marie Journal of the Chemical Society, Chemical Communications, Issue 22 https://doi.org/10.1039/c39910001589	journal	January 1991
Well-defined azazirconacyclopropane complexes supported on silica structurally determined by 2D NMR comparative elucidation Eter, Mohamad El; Hamzaoui, Bilel; Abou-Hamad, Edy Chemical Communications, Vol. 49, Issue 41 https://doi.org/10.1039/c3cc40385h	journal	January 2013
Selective reduction of CO ₂ to a methanol equivalent by B(C ₆ F ₅ ) ₃ -activated alkaline earth catalysis Anker, Mathew D.; Arrowsmith, Merle; Bellham, Peter Chem. Sci., Vol. 5, Issue 7 https://doi.org/10.1039/c4sc00885e	journal	January 2014
Theoretical and experimental assessment of single- and multiple-quantum cross-polarization in solid state NMR Amoureux, J. -P.; Pruski, M. Molecular Physics, Vol. 100, Issue 10 https://doi.org/10.1080/00268970210125755	journal	May 2002
Supported Organometallic Catalysts for Olefin Polymerization Zakharov, V. A.; Yermakov, Yu. I. Catalysis Reviews, Vol. 19, Issue 1 https://doi.org/10.1080/03602457908065101	journal	January 1979
Efficient pseudopotentials for plane-wave calculations Troullier, N.; Martins, José Luriaas Physical Review B, Vol. 43, Issue 3 https://doi.org/10.1103/PhysRevB.43.1993	journal	January 1991
Enantioselective hydrosilation of ketones in the presence of an S , S -[1,2-bis(tetrahydroindenyl)ethane]-titanium catalyst Xin, Shixuan; Harrod, John F. Canadian Journal of Chemistry, Vol. 73, Issue 7 https://doi.org/10.1139/v95-123	journal	July 1995

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
carbonyl hydroboration
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Title: Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration

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