Supported Single-Site Ti(IV) on a Metal–Organic Framework for the Hydroboration of Carbonyl Compounds

Huang, Zhiyuan; Liu, Dong; Camacho-Bunquin, Jeffrey; Zhang, Guanghui; Yang, Dali; Lopez-Encarnacion, Juan M.; Xu, Yunjie; Ferrandon, Magali S.; Niklas, Jens; Poluektov, Oleg G.; Jellinek, Julius; Lei, Aiwen; Bunel, Emilio E.; Delferro, Massimiliano

doi:10.1021/acs.organomet.7b00544

Title: Supported Single-Site Ti(IV) on a Metal–Organic Framework for the Hydroboration of Carbonyl Compounds

Journal Article · Thu Oct 12 00:00:00 EDT 2017 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.7b00544· OSTI ID:1422836

Huang, Zhiyuan ^[1]; Liu, Dong ^[1];

^[2];

^[3]; Yang, Dali ^[1]; Lopez-Encarnacion, Juan M. ^[4]; Xu, Yunjie ^[3]; Ferrandon, Magali S. ^[2];

^[2]; Poluektov, Oleg G. ^[2];

^[2];

^[1]; Bunel, Emilio E. ^[2];

^[2]

Wuhan Univ., Wuhan (People's Republic of China); Argonne National Lab. (ANL), Lemont, IL (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)
Illinois Institute of Technology, Chicago, IL (United States)
Argonne National Lab. (ANL), Lemont, IL (United States); Univ. of Puerto Rico at Cayey, Cayey, Puerto Rico (United States)

Here, a stable and structurally well-defined titanium alkoxide catalyst supported on a metal-organic-framework (MOF) of UiO-67 topology (ANL1-Ti(OⁱPr)₂) was synthesized and fully characterized by a variety of analytical and spectroscopic techniques, including BET, TGA, PXRD, XAS, DRIFT, SEM, and DFT computations. The Ti-functionalized MOF was demonstrated active for the catalytic hydroboration of a wide range of aldehydes and ketones with HBpin as the boron source. Compared to traditional homogeneous and supported hydroboration catalysts, ANL1-Ti(OⁱPr)₂ is completely recyclable and reusable, making it a promising hydroboration catalyst alternative for green and sustainable chemical synthesis. DFT calculations suggest that the catalytic hydroboration proceeds via a (1) hydride transfer between the active Ti-hydride species and a carbonyl moiety (rate determining step), and (2) alkoxide transfer (intramolecular σ-bond metathesis) to generate the boronate ester product.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1422836

Journal Information:: Organometallics, Vol. 36, Issue 20; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 41 works

Citation information provided by
Web of Science

References (90)

Catalysis for Total Synthesis: A Personal Account Fürstner, Alois Angewandte Chemie International Edition, Vol. 53, Issue 33 https://doi.org/10.1002/anie.201402719	journal	July 2014
Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance Nicolaou, K. C.; Hale, Christopher R. H.; Nilewski, Christian Chemical Society Reviews, Vol. 41, Issue 15 https://doi.org/10.1039/c2cs35116a	journal	January 2012
Merging Chemical Synthesis and Biosynthesis: A New Chapter in the Total Synthesis of Natural Products and Natural Product Libraries Kirschning, Andreas; Hahn, Frank Angewandte Chemie International Edition, Vol. 51, Issue 17 https://doi.org/10.1002/anie.201107386	journal	March 2012
“Common synthetic scaffolds” in the synthesis of structurally diverse natural products Anagnostaki, Elissavet E.; Zografos, Alexandros L. Chemical Society Reviews, Vol. 41, Issue 17 https://doi.org/10.1039/c2cs35080g	journal	January 2012
Chemoselectivity: The Mother of Invention in Total Synthesis Shenvi, Ryan A.; O’Malley, Daniel P.; Baran, Phil S. Accounts of Chemical Research, Vol. 42, Issue 4 https://doi.org/10.1021/ar800182r	journal	April 2009
The art of total synthesis through cascade reactions Nicolaou, K. C.; Chen, Jason S. Chemical Society Reviews, Vol. 38, Issue 11 https://doi.org/10.1039/b903290h	journal	January 2009
Synthesis of Natural Product Inspired Compound Collections Kumar, Kamal; Waldmann, Herbert Angewandte Chemie International Edition, Vol. 48, Issue 18 https://doi.org/10.1002/anie.200803437	journal	April 2009
Transition-metal promoted hydroborations of alkenes, emerging methodology for organic transformations Burgess, Kevin.; Ohlmeyer, Michael J. Chemical Reviews, Vol. 91, Issue 6 https://doi.org/10.1021/cr00006a003	journal	September 1991
Nickel N-Heterocyclic Carbene-Catalyzed C–Heteroatom Bond Formation, Reduction, and Oxidation: Reactions and Mechanistic Aspects Ritleng, Vincent; Henrion, Mickaël; Chetcuti, Michael J. ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b02021	journal	January 2016
Catalytic Reduction by Quasi-Homogeneous Gold Nanoclusters in the Liquid Phase Chong, Hanbao; Zhu, Manzhou ChemCatChem, Vol. 7, Issue 15 https://doi.org/10.1002/cctc.201500247	journal	July 2015
Nickel and Iron Pincer Complexes as Catalysts for the Reduction of Carbonyl Compounds Chakraborty, Sumit; Bhattacharya, Papri; Dai, Huiguang Accounts of Chemical Research, Vol. 48, Issue 7 https://doi.org/10.1021/acs.accounts.5b00055	journal	June 2015
Stereoselectivity in the reduction of ketones by metal hydrides Ayres, D. C.; Sawdaye, R. Chemical Communications (London), Issue 15 https://doi.org/10.1039/c19660000527	journal	January 1966
Stereochemistry of the Lithium Aluminum Hydride Reduction of Ketones Umland, Jean Blanchard; Jefraim, Margaret I. Journal of the American Chemical Society, Vol. 78, Issue 12 https://doi.org/10.1021/ja01593a037	journal	June 1956
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
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
Magnesium Catalysis of Imine Hydroboration Arrowsmith, Merle; Hill, Michael S.; Kociok-Köhn, Gabriele Chemistry - A European Journal, Vol. 19, Issue 8 https://doi.org/10.1002/chem.201203190	journal	January 2013
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
Enantioselective Reduction of Prochiral Ketones by Catecholborane Catalysed by Chiral Group 13 Complexes Blake, Alexander J.; Cunningham, Anthony; Ford, Alan Chemistry - A European Journal, Vol. 6, Issue 19 https://doi.org/10.1002/1521-3765(20001002)6:19<3586::AID-CHEM3586>3.0.CO;2-S	journal	October 2000
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
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
Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst Dudnik, Alexander S.; Weidner, Victoria L.; Motta, Alessandro Nature Chemistry, Vol. 6, Issue 12 https://doi.org/10.1038/nchem.2087	journal	October 2014
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
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
Ring‐Shaped Phosphinoamido‐Magnesium‐Hydride Complexes: Syntheses, Structures, Reactivity, and Catalysis Fohlmeister, Lea; Stasch, Andreas Chemistry – A European Journal, Vol. 22, Issue 29 https://doi.org/10.1002/chem.201601623	journal	June 2016
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
Chiral Titanium Alkoxides as Catalysts for the Enantioselective Reduction of Ketones with Boranes Giffels, Guido; Dreisbach, Claus; Kragl, Udo Angewandte Chemie International Edition in English, Vol. 34, Issue 18 https://doi.org/10.1002/anie.199520051	journal	October 1995
Metal alkoxide catalysis of catecholborane and borane reductions. Mechanistic studies Lindsley, Craig W.; DiMare, Marcello Tetrahedron Letters, Vol. 35, Issue 29 https://doi.org/10.1016/S0040-4039(00)77048-1	journal	July 1994
A Boron-Substituted Analogue of the Shvo Hydrogenation Catalyst: Catalytic Hydroboration of Aldehydes, Imines, and Ketones Koren-Selfridge, Liza; Londino, Hannah N.; Vellucci, Jessica K. Organometallics, Vol. 28, Issue 7 https://doi.org/10.1021/om801228m	journal	April 2009
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
Zinc triflate–bis-oxazoline complexes as chiral catalysts: enantioselective reduction of α-alkoxy-ketones with catecholborane Bandini, Marco; Cozzi, Pier Giorgio; de Angelis, Meri Tetrahedron Letters, Vol. 41, Issue 10 https://doi.org/10.1016/S0040-4039(99)02339-4	journal	March 2000
σ-Bond Metathesis: A 30-Year Retrospective Waterman, Rory Organometallics, Vol. 32, Issue 24 https://doi.org/10.1021/om400760k	journal	September 2013
The σ-CAM Mechanism: σ Complexes as the Basis of σ-Bond Metathesis at Late-Transition-Metal Centers Perutz, Robin N.; Sabo-Etienne, Sylviane Angewandte Chemie International Edition, Vol. 46, Issue 15 https://doi.org/10.1002/anie.200603224	journal	April 2007
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
Catalysis by Design: Well-Defined Single-Site Heterogeneous Catalysts Pelletier, Jérémie D. A.; Basset, Jean-Marie Accounts of Chemical Research, Vol. 49, Issue 4 https://doi.org/10.1021/acs.accounts.5b00518	journal	March 2016
Isolated Surface Hydrides: Formation, Structure, and Reactivity Copéret, Christophe; Estes, Deven P.; Larmier, Kim Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00082	journal	June 2016
Surface Organometallic and Coordination Chemistry toward Single-Site Heterogeneous Catalysts: Strategies, Methods, Structures, and Activities Copéret, Christophe; Comas-Vives, Aleix; Conley, Matthew P. Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00373	journal	January 2016
Molecular Metal Catalysts on Supports: Organometallic Chemistry Meets Surface Science Serna, Pedro; Gates, Bruce C. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500170k	journal	July 2014
Catalysis and Surface Organometallic Chemistry: A View from Theory and Simulations Sautet, Philippe; Delbecq, Françoise Chemical Reviews, Vol. 110, Issue 3 https://doi.org/10.1021/cr900295b	journal	March 2010
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
Correlating Synthetic Methods, Morphology, Atomic-Level Structure, and Catalytic Activity of Sn-β Catalysts Wolf, Patrick; Valla, Maxence; Núñez-Zarur, Francisco ACS Catalysis, Vol. 6, Issue 7 https://doi.org/10.1021/acscatal.6b00114	journal	May 2016
Identifying low-coverage surface species on supported noble metal nanoparticle catalysts by DNP-NMR Johnson, Robert L.; Perras, Frédéric A.; Kobayashi, Takeshi Chemical Communications, Vol. 52, Issue 9 https://doi.org/10.1039/C5CC06788J	journal	January 2016
Atomic Description of the Interface between Silica and Alumina in Aluminosilicates through Dynamic Nuclear Polarization Surface-Enhanced NMR Spectroscopy and First-Principles Calculations Valla, Maxence; Rossini, Aaron J.; Caillot, Maxime Journal of the American Chemical Society, Vol. 137, Issue 33 https://doi.org/10.1021/jacs.5b06134	journal	August 2015
NMR Signatures of the Active Sites in Sn-β Zeolite Wolf, Patrick; Valla, Maxence; Rossini, Aaron J. Angewandte Chemie International Edition, Vol. 53, Issue 38 https://doi.org/10.1002/anie.201403905	journal	July 2014
Silica-surface reorganization during organotin grafting evidenced by ¹¹⁹ Sn DNP SENS: a tandem reaction of gem-silanols and strained siloxane bridges Conley, Matthew P.; Rossini, Aaron J.; Comas-Vives, Aleix Phys. Chem. Chem. Phys., Vol. 16, Issue 33 https://doi.org/10.1039/C4CP01973C	journal	January 2014
High resolution solid state NMRspectroscopy in surface organometallic chemistry: access to molecular understanding of active sites of well-defined heterogeneous catalysts Blanc, Frédéric; Copéret, Christophe; Lesage, Anne Chem. Soc. Rev., Vol. 37, Issue 3 https://doi.org/10.1039/B612793M	journal	January 2008
Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration Eedugurala, Naresh; Wang, Zhuoran; Chaudhary, Umesh ACS Catalysis, Vol. 5, Issue 12 https://doi.org/10.1021/acscatal.5b01671	journal	November 2015
Metal–Organic Framework Nodes Support Single-Site Magnesium–Alkyl Catalysts for Hydroboration and Hydroamination Reactions Manna, Kuntal; Ji, Pengfei; Greene, Francis X. Journal of the American Chemical Society, Vol. 138, Issue 24 https://doi.org/10.1021/jacs.6b03689	journal	June 2016
Best Practices for the Synthesis, Activation, and Characterization of Metal–Organic Frameworks Howarth, Ashlee J.; Peters, Aaron W.; Vermeulen, Nicolaas A. Chemistry of Materials, Vol. 29, Issue 1 https://doi.org/10.1021/acs.chemmater.6b02626	journal	September 2016
Metal–organic framework materials for light-harvesting and energy transfer So, Monica C.; Wiederrecht, Gary P.; Mondloch, Joseph E. Chemical Communications, Vol. 51, Issue 17 https://doi.org/10.1039/C4CC09596K	journal	January 2015
Solvent-Assisted Linker Exchange: An Alternative to the De Novo Synthesis of Unattainable Metal-Organic Frameworks Karagiaridi, Olga; Bury, Wojciech; Mondloch, Joseph E. Angewandte Chemie International Edition, Vol. 53, Issue 18 https://doi.org/10.1002/anie.201306923	journal	March 2014
Beyond post-synthesis modification: evolution of metal–organic frameworks via building block replacement Deria, Pravas; Mondloch, Joseph E.; Karagiaridi, Olga Chem. Soc. Rev., Vol. 43, Issue 16 https://doi.org/10.1039/C4CS00067F	journal	January 2014
Metal–Organic Framework Materials as Chemical Sensors Kreno, Lauren E.; Leong, Kirsty; Farha, Omar K. Chemical Reviews, Vol. 112, Issue 2, p. 1105-1125 https://doi.org/10.1021/cr200324t	journal	September 2011
Doping Metal–Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis Wang, Cheng; Xie, Zhigang; deKrafft, Kathryn E. Journal of the American Chemical Society, Vol. 133, Issue 34, p. 13445-13454 https://doi.org/10.1021/ja203564w	journal	August 2011
Rational Design, Synthesis, Purification, and Activation of Metal−Organic Framework Materials Farha, Omar K.; Hupp, Joseph T. Accounts of Chemical Research, Vol. 43, Issue 8, p. 1166-1175 https://doi.org/10.1021/ar1000617	journal	August 2010
Metal–organic framework materials as catalysts Lee, JeongYong; Farha, Omar K.; Roberts, John Chemical Society Reviews, Vol. 38, Issue 5, p. 1450-1459 https://doi.org/10.1039/b807080f	journal	January 2009
A Homochiral Porous Metal−Organic Framework for Highly Enantioselective Heterogeneous Asymmetric Catalysis Wu, Chuan-De; Hu, Aiguo; Zhang, Lin Journal of the American Chemical Society, Vol. 127, Issue 25 https://doi.org/10.1021/ja052431t	journal	June 2005
Isolated, well-defined organovanadium( iii ) on silica: single-site catalyst for hydrogenation of alkenes and alkynes Sohn, H.; Camacho-Bunquin, J.; Langeslay, R. R. Chemical Communications, Vol. 53, Issue 53 https://doi.org/10.1039/C7CC01876B	journal	January 2017
Supported Aluminum Catalysts for Olefin Hydrogenation Camacho-Bunquin, Jeffrey; Ferrandon, Magali; Das, Ujjal ACS Catalysis, Vol. 7, Issue 1 https://doi.org/10.1021/acscatal.6b02771	journal	December 2016
Metal–organic frameworks: versatile heterogeneous catalysts for efficient catalytic organic transformations Chughtai, Adeel H.; Ahmad, Nazir; Younus, Hussein A. Chemical Society Reviews, Vol. 44, Issue 19 https://doi.org/10.1039/C4CS00395K	journal	January 2015
Applications of metal–organic frameworks in heterogeneous supramolecular catalysis Liu, Jiewei; Chen, Lianfen; Cui, Hao Chemical Society Reviews, Vol. 43, Issue 16, p. 6011-6061 https://doi.org/10.1039/C4CS00094C	journal	January 2014
Porous Metal–Organic Frameworks for Heterogeneous Biomimetic Catalysis Zhao, Min; Ou, Sha; Wu, Chuan-De Accounts of Chemical Research, Vol. 47, Issue 4, p. 1199-1207 https://doi.org/10.1021/ar400265x	journal	February 2014
Homochiral Metal–Organic Frameworks for Asymmetric Heterogeneous Catalysis Yoon, Minyoung; Srirambalaji, Renganathan; Kim, Kimoon Chemical Reviews, Vol. 112, Issue 2, p. 1196-1231 https://doi.org/10.1021/cr2003147	journal	September 2011
Chemoselective single-site Earth-abundant metal catalysts at metal–organic framework nodes Manna, Kuntal; Ji, Pengfei; Lin, Zekai Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12610	journal	August 2016
Single-Site Cobalt Catalysts at New Zr ₈ (μ ₂ -O) ₈ (μ ₂ -OH) ₄ Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles Ji, Pengfei; Manna, Kuntal; Lin, Zekai Journal of the American Chemical Society, Vol. 138, Issue 37 https://doi.org/10.1021/jacs.6b06759	journal	September 2016
Single-Site Organozirconium Catalyst Embedded in a Metal–Organic Framework Klet, Rachel C.; Tussupbayev, Samat; Borycz, Joshua Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11350	journal	December 2015
Tuning Zr ₆ Metal–Organic Framework (MOF) Nodes as Catalyst Supports: Site Densities and Electron-Donor Properties Influence Molecular Iridium Complexes as Ethylene Conversion Catalysts Yang, Dong; Odoh, Samuel O.; Borycz, Joshua ACS Catalysis, Vol. 6, Issue 1 https://doi.org/10.1021/acscatal.5b02243	journal	December 2015
Tailoring the Pore Size and Functionality of UiO-Type Metal–Organic Frameworks for Optimal Nerve Agent Destruction Peterson, Gregory W.; Moon, Su-Young; Wagner, George W. Inorganic Chemistry, Vol. 54, Issue 20 https://doi.org/10.1021/acs.inorgchem.5b01867	journal	October 2015
Effective, Facile, and Selective Hydrolysis of the Chemical Warfare Agent VX Using Zr ₆ -Based Metal–Organic Frameworks Moon, Su-Young; Wagner, George W.; Mondloch, Joseph E. Inorganic Chemistry, Vol. 54, Issue 22 https://doi.org/10.1021/acs.inorgchem.5b01813	journal	October 2015
One Step Backward Is Two Steps Forward: Enhancing the Hydrolysis Rate of UiO-66 by Decreasing [OH ^– ] Katz, Michael J.; Klet, Rachel C.; Moon, Su-Young ACS Catalysis, Vol. 5, Issue 8 https://doi.org/10.1021/acscatal.5b00785	journal	July 2015
A mixed dicarboxylate strut approach to enhancing catalytic activity of a de novo urea derivative of metal–organic framework UiO-67 Siu, Paul W.; Brown, Zachary J.; Farha, Omar K. Chemical Communications, Vol. 49, Issue 93 https://doi.org/10.1039/c3cc47177b	journal	January 2013
A facile synthesis of UiO-66, UiO-67 and their derivatives Katz, Michael J.; Brown, Zachary J.; Colón, Yamil J. Chemical Communications, Vol. 49, Issue 82 https://doi.org/10.1039/c3cc46105j	journal	January 2013
Synthesis and characterization of a monomeric octahedral C2-symmetric titanium complex bearing two 3,3′-diphenyl-2,2′-biphenol ligands Diebold, Carine; Mobian, Pierre; Huguenard, Clarisse Dalton Transactions, Issue 46 https://doi.org/10.1039/b912694p	journal	January 2009
Comparative study of titanium-functionalized UiO-66: support effect on the oxidation of cyclohexene using hydrogen peroxide Nguyen, Huong Giang T.; Mao, Lily; Peters, Aaron W. Catalysis Science & Technology, Vol. 5, Issue 9 https://doi.org/10.1039/C5CY00825E	journal	January 2015
XANES and EXAFS study of titanium alkoxides Babonneau, F.; Doeuff, S.; Leaustic, A. Inorganic Chemistry, Vol. 27, Issue 18 https://doi.org/10.1021/ic00291a024	journal	September 1988
A XANES and EXAFS investigation of titanium silicalite Behrens, Peter; Felsche, J�rgen; Vetter, Sabina Journal of the Chemical Society, Chemical Communications, Issue 10 https://doi.org/10.1039/c39910000678	journal	January 1991
Titanium sites in titanium silicalites: An XPS, XANES and EXAFS study On, D. Trong; Bonneviot, L.; Bittar, A. Journal of Molecular Catalysis, Vol. 74, Issue 1-3 https://doi.org/10.1016/0304-5102(92)80241-8	journal	July 1992
Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds Kaithal, Akash; Chatterjee, Basujit; Gunanathan, Chidambaram Organic Letters, Vol. 17, Issue 19 https://doi.org/10.1021/acs.orglett.5b02352	journal	September 2015
C−H Activation for the Construction of C−B Bonds Mkhalid, Ibraheem A. I.; Barnard, Jonathan H.; Marder, Todd B. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900206p	journal	February 2010
Titanocene-Catalyzed Hydrosilylation of Imines: Experimental and Computational Investigations of the Catalytically Active Species Gruber-Woelfler, Heidrun; Khinast, Johannes G.; Flock, Michaela Organometallics, Vol. 28, Issue 8 https://doi.org/10.1021/om800643q	journal	March 2009
First Titanium-Catalyzed a nti -1,4-Hydrosilylation of Dienes Bareille, Laurianne; Becht, Sabine; Cui, Jin Lan Organometallics, Vol. 24, Issue 24 https://doi.org/10.1021/om050533m	journal	November 2005
Bis(oxazoline)titanium Complexes as Chiral Catalysts for Enantioselective Hydrosilylation of Ketones − A Combined Experimental and Theoretical Investigation Bandini, Marco; Bernardi, Fernando; Bottoni, Andrea European Journal of Organic Chemistry, Vol. 2003, Issue 15 https://doi.org/10.1002/ejoc.200200675	journal	August 2003
Density Functional Theory Studies of Titanium-Catalyzed Hydroboration of Olefins Liu, Dan; Lin, Zhenyang Organometallics, Vol. 21, Issue 22 https://doi.org/10.1021/om020326b	journal	October 2002
Homogeneous Catalytic Hydrosilylation of Pyridines Hao, Leijun; Harrod, John F.; Lebuis, Anne-Marie Angewandte Chemie International Edition, Vol. 37, Issue 22 https://doi.org/10.1002/(SICI)1521-3773(19981204)37:22<3126::AID-ANIE3126>3.0.CO;2-Q	journal	December 1998
A catalytic method for the reduction of esters to alcohols Berk, Scott C.; Kreutzer, Kristina A.; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 113, Issue 13 https://doi.org/10.1021/ja00013a074	journal	June 1991
Natural hybrid orbitals Foster, J. P.; Weinhold, F. Journal of the American Chemical Society, Vol. 102, Issue 24 https://doi.org/10.1021/ja00544a007	journal	September 1980
Safe and Convenient Procedure for Solvent Purification Pangborn, Amy B.; Giardello, Michael A.; Grubbs, Robert H. Organometallics, Vol. 15, Issue 5, p. 1518-1520 https://doi.org/10.1021/om9503712	journal	January 1996
Control of framework interpenetration for in situ modified hydroxyl functionalised IRMOFs Rankine, Damien; Avellaneda, Antonio; Hill, Matthew R. Chemical Communications, Vol. 48, Issue 83 https://doi.org/10.1039/c2cc35565e	journal	January 2012
NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations Valiev, M.; Bylaska, E. J.; Govind, N. Computer Physics Communications, Vol. 181, Issue 9, p. 1477-1489 https://doi.org/10.1016/j.cpc.2010.04.018	journal	September 2010
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
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310 https://doi.org/10.1063/1.448975	journal	January 1985

Cited By (10)

Iron( ii ) coordination polymer catalysed hydroboration of ketones Li, Li; Liu, E.; Cheng, Jessica Dalton Transactions, Vol. 47, Issue 29 https://doi.org/10.1039/c8dt02134a	journal	January 2018
Novel aluminium compounds derived from Schiff bases: Synthesis, characterization and catalytic performance in hydroboration: Synthesis, Characterization and Catalytic Performance of Al Compounds Jin, Da; Ma, Xiaoli; Liu, Yashuai Applied Organometallic Chemistry, Vol. 33, Issue 3 https://doi.org/10.1002/aoc.4637	journal	January 2019
Highly efficient hydroboration of carbonyl compounds catalyzed by tris(methylcyclopentadienyl)lanthanide complexes Yan, Dandan; Dai, Ping; Chen, Sufang Organic & Biomolecular Chemistry, Vol. 16, Issue 15 https://doi.org/10.1039/c8ob00292d	journal	January 2018
Hydroboration, Cyanosilylation, and Sequential Cyanosilylation and Hydroboration of Carbonyl Compounds in the Presence of a Ti ^IV Amido Complex as an Efficient Catalyst : Hydroboration, Cyanosilylation, and Sequential Cyanosilylation and Hydroboration of Carbonyl Compounds in the Presence of a TiIV Amido Complex as an E Harinath, Adimulam; Bhattcharjee, Jayeeta; Gorantla, Koteswar Rao European Journal of Organic Chemistry, Vol. 2018, Issue 24 https://doi.org/10.1002/ejoc.201800547	journal	June 2018
Reusable Fe ₂ O ₃ -nanoparticle catalysed efficient and selective hydroboration of carbonyl compounds Shegavi, Mahadev L.; Baishya, Ashim; Geetharani, K. Organic Chemistry Frontiers, Vol. 5, Issue 24 https://doi.org/10.1039/c8qo00912k	journal	January 2018
Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage Patnaik, Smita; Sadow, Aaron D. Angewandte Chemie, Vol. 131, Issue 8 https://doi.org/10.1002/ange.201813305	journal	January 2019
Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage Patnaik, Smita; Sadow, Aaron D. Angewandte Chemie International Edition, Vol. 58, Issue 8 https://doi.org/10.1002/anie.201813305	journal	February 2019
Recent advances in the catalytic hydroboration of carbonyl compounds Shegavi, Mahadev L.; Bose, Shubhankar Kumar Catalysis Science & Technology, Vol. 9, Issue 13 https://doi.org/10.1039/c9cy00807a	journal	January 2019
Highly efficient and selective hydroboration of terminal and internal alkynes catalysed by a cobalt( ii ) coordination polymer Zhang, Guoqi; Li, Sihan; Wu, Jing Organic Chemistry Frontiers, Vol. 6, Issue 18 https://doi.org/10.1039/c9qo00834a	journal	January 2019
Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds Harinath, Adimulam; Bhattacharjee, Jayeeta; Nayek, Hari Pada Dalton Transactions, Vol. 47, Issue 36 https://doi.org/10.1039/c8dt02032a	journal	January 2018

Similar Records

Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration

Journal Article · Wed Nov 04 00:00:00 EST 2015 · ACS Catalysis · OSTI ID:1422836

Eedugurala, Naresh; Wang, Zhuoran; Chaudhary, Umesh; +6 more

Aldehyde and Ketone Hydroboration Mediated by a Heterogeneous Single‐Site Molybdenum‐Dioxo Catalyst: Scope and Mechanistic Implications

Journal Article · Mon Jan 22 00:00:00 EST 2024 · ChemCatChem · OSTI ID:1422836

Liu, Yiqi; Agarwal, Amol; Ye, Liwei; +2 more

Single-Site Cobalt Catalysts at New Zr ₈ (μ ₂ -O) ₈ (μ ₂ -OH) ₄ Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles

Journal Article · Wed Sep 21 00:00:00 EDT 2016 · Journal of the American Chemical Society · OSTI ID:1422836

Ji, Pengfei; Manna, Kuntal; Lin, Zekai; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Supported Single-Site Ti(IV) on a Metal–Organic Framework for the Hydroboration of Carbonyl Compounds

Citation Formats

References (90)

Cited By (10)

Similar Records

Related Subjects