Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)

Taylor, Mercedes K.; Juhl, Martin; Hadaf, Gul Barg; Hwang, Dasol; Velasquez, Ever; Oktawiec, Julia; Lefton, Jonathan B.; Runčevski, Tomče; Long, Jeffrey R.; Lee, Ji-Woong

doi:10.1039/C9CC08614E

Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)

Journal Article · Mon Jan 27 23:00:00 EST 2020 · ChemComm

DOI:https://doi.org/10.1039/C9CC08614E· OSTI ID:1581029

^[1]; Juhl, Martin ^[2]; Hadaf, Gul Barg ^[2]; Hwang, Dasol ^[2]; Velasquez, Ever ^[3]; Oktawiec, Julia ^[4]; Lefton, Jonathan B. ^[5]; Runčevski, Tomče ^[5]; ^[6]; ^[2]

Center for Integrated Nanotechnologies, Sandia National Laboratories, Albuquerque, USA, Department of Chemistry
Department of Chemistry & Nano-Science Center, University of Copenhagen, Denmark
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, USA, Department of Chemical and Biomolecular Engineering
Department of Chemistry, University of California, Berkeley, USA
Department of Chemistry, Southern Methodist University, USA
Department of Chemistry, University of California, Berkeley, USA, Materials Sciences Division

A facile catalytic protocol achieves the homocoupling of pyrazole boronic esters, enabling access to the structurally-flexible metal–organic framework Co(bpz).

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC02-06CH11357; AC02-05CH11231; NA0003525

OSTI ID:: 1581029

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 8 Vol. 56; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (42)

Porous Coordination-Polymer Crystals with Gated Channels Specific for Supercritical Gases Kitaura, Ryo; Seki, Kenji; Akiyama, George Angewandte Chemie International Edition, Vol. 42, Issue 4 https://doi.org/10.1002/anie.200390130	journal	January 2003
4,4′-Bipyrazolyl: new bitopic connector for construction of coordination networks Boldog, Ishtvan; Sieler, Joachim; Chernega, Alexander N. Inorganica Chimica Acta, Vol. 338 https://doi.org/10.1016/S0020-1693(02)00902-7	journal	October 2002
3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1 Pelcman, Benjamin; Sanin, Andrei; Nilsson, Peter Bioorganic & Medicinal Chemistry Letters, Vol. 25, Issue 15 https://doi.org/10.1016/j.bmcl.2015.05.004	journal	August 2015
Coordination polymers and metal–organic frameworks based on poly(pyrazole)-containing ligands Pettinari, Claudio; Tăbăcaru, Aurel; Galli, Simona Coordination Chemistry Reviews, Vol. 307 https://doi.org/10.1016/j.ccr.2015.08.005	journal	January 2016
The therapeutic voyage of pyrazole and its analogs: A review Khan, Mohemmed Faraz; Alam, Mohammad Mumtaz; Verma, Garima European Journal of Medicinal Chemistry, Vol. 120 https://doi.org/10.1016/j.ejmech.2016.04.077	journal	September 2016
Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety Taydakov, Ilya V.; Akkuzina, Alina A.; Avetisov, Roman I. Journal of Luminescence, Vol. 177 https://doi.org/10.1016/j.jlumin.2016.04.017	journal	September 2016
Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium Lee, Kooyeon; Lee, Phil Ho Tetrahedron Letters, Vol. 49, Issue 27 https://doi.org/10.1016/j.tetlet.2008.04.123	journal	June 2008
Single-Crystal to Single-Crystal Transformation of a Nonporous Fe(II) Metal–Organic Framework into a Porous Metal–Organic Framework via a Solid-State Reaction Spirkl, Sebastian; Grzywa, Maciej; Reschke, Stephan Inorganic Chemistry, Vol. 56, Issue 20 https://doi.org/10.1021/acs.inorgchem.7b01818	journal	September 2017
The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction Jedinák, Lukáš; Zátopková, Renáta; Zemánková, Hana The Journal of Organic Chemistry, Vol. 82, Issue 1 https://doi.org/10.1021/acs.joc.6b02306	journal	December 2016
Synthesis of N -Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives Onodera, Shunsuke; Kochi, Takuya; Kakiuchi, Fumitoshi The Journal of Organic Chemistry, Vol. 84, Issue 10 https://doi.org/10.1021/acs.joc.9b00673	journal	April 2019
Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles Tu, Kim N.; Kim, Scott; Blum, Suzanne A. Organic Letters, Vol. 21, Issue 5 https://doi.org/10.1021/acs.orglett.8b04038	journal	February 2019
Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N -Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles Yi, Fanhua; Zhao, Wanjun; Wang, Zikun Organic Letters, Vol. 21, Issue 9 https://doi.org/10.1021/acs.orglett.9b00860	journal	April 2019
Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction Hassan, Jwanro; Sévignon, Marc; Gozzi, Christel Chemical Reviews, Vol. 102, Issue 5, p. 1359-1470 https://doi.org/10.1021/cr000664r	journal	May 2002
From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles Fustero, Santos; Sánchez-Roselló, María; Barrio, Pablo Chemical Reviews, Vol. 111, Issue 11 https://doi.org/10.1021/cr2000459	journal	November 2011
Metal–Organic Frameworks for Separations Li, Jian-Rong; Sculley, Julian; Zhou, Hong-Cai Chemical Reviews, Vol. 112, Issue 2, p. 869-932 https://doi.org/10.1021/cr200190s	journal	September 2011
Coordination chemistry of pyrazole-derived ligands Trofimenko, Swiatoslaw. Chemical Reviews, Vol. 72, Issue 5 https://doi.org/10.1021/cr60279a003	journal	October 1972
Photophysical and Electrochemical Properties of Heteroleptic Tris-Cyclometalated Iridium(III) Complexes Dedeian, Kenneth; Shi, Jianmin; Shepherd, Nigel Inorganic Chemistry, Vol. 44, Issue 13 https://doi.org/10.1021/ic050324u	journal	June 2005
Novel Coordination Frameworks Incorporating the 4,4′-Bipyrazolyl Ditopic Ligand Pettinari, Claudio; Tăbăcaru, Aurel; Boldog, Ishtvan Inorganic Chemistry, Vol. 51, Issue 9 https://doi.org/10.1021/ic3001416	journal	April 2012
Raman and IR Studies of Pressure- and Temperature-Induced Phase Transitions in [(CH 2 ) 3 NH 2 ][Zn(HCOO) 3 ] Mączka, Mirosław; da Silva, Tercio Almeida; Paraguassu, Waldeci Inorganic Chemistry, Vol. 53, Issue 23 https://doi.org/10.1021/ic502426x	journal	November 2014
Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids: Key Involvement of a Palladium Peroxo Complex Adamo, Carlo; Amatore, Christian; Ciofini, Ilaria Journal of the American Chemical Society, Vol. 128, Issue 21 https://doi.org/10.1021/ja0569959	journal	May 2006
Tetrahedral Zinc Complexes with Liquid Crystalline and Luminescent Properties: Interplay Between Nonconventional Molecular Shapes and Supramolecular Mesomorphic Order Cavero, Emma; Uriel, Santiago; Romero, Pilar Journal of the American Chemical Society, Vol. 129, Issue 37 https://doi.org/10.1021/ja073639c	journal	September 2007
Tuning the Adsorption Properties of Isoreticular Pyrazolate-Based Metal–Organic Frameworks through Ligand Modification Colombo, Valentina; Montoro, Carmen; Maspero, Angelo Journal of the American Chemical Society, Vol. 134, Issue 30 https://doi.org/10.1021/ja305267m	journal	July 2012
Broadly Hysteretic H ₂ Adsorption in the Microporous Metal−Organic Framework Co(1,4-benzenedipyrazolate) Choi, Hye Jin; Dincă, Mircea; Long, Jeffrey R. Journal of the American Chemical Society, Vol. 130, Issue 25 https://doi.org/10.1021/ja8024092	journal	June 2008
Thermodynamics of Guest-Induced Structural Transitions in Hybrid Organic−Inorganic Frameworks Coudert, François-Xavier; Jeffroy, Marie; Fuchs, Alain H. Journal of the American Chemical Society, Vol. 130, Issue 43 https://doi.org/10.1021/ja805129c	journal	October 2008
Complex Adsorption of Short Linear Alkanes in the Flexible Metal-Organic-Framework MIL-53(Fe) Llewellyn, P. L.; Horcajada, P.; Maurin, G. Journal of the American Chemical Society, Vol. 131, Issue 36 https://doi.org/10.1021/ja902740r	journal	September 2009
Tuning the Adsorption-Induced Phase Change in the Flexible Metal–Organic Framework Co(bdp) Taylor, Mercedes K.; Runčevski, Tomče; Oktawiec, Julia Journal of the American Chemical Society, Vol. 138, Issue 45 https://doi.org/10.1021/jacs.6b09155	journal	November 2016
Near-Perfect CO 2 /CH 4 Selectivity Achieved through Reversible Guest Templating in the Flexible Metal–Organic Framework Co(bdp) Taylor, Mercedes K.; Runčevski, Tomče; Oktawiec, Julia Journal of the American Chemical Society, Vol. 140, Issue 32 https://doi.org/10.1021/jacs.8b06062	journal	July 2018
Influence of Metal Substitution on the Pressure-Induced Phase Change in Flexible Zeolitic Imidazolate Frameworks McGuirk, C. Michael; Runčevski, Tomče; Oktawiec, Julia Journal of the American Chemical Society, Vol. 140, Issue 46 https://doi.org/10.1021/jacs.8b09631	journal	November 2018
N-Dealkylation of pyrazoles using pyridine hydrochloride Butler, Donald E.; DeWald, Horace A. The Journal of Organic Chemistry, Vol. 40, Issue 9 https://doi.org/10.1021/jo00897a041	journal	May 1975
1,1,2,2-Ethanetetracarboxaldehyde and Its Reactions Trofimenko, S. The Journal of Organic Chemistry, Vol. 29, Issue 10 https://doi.org/10.1021/jo01033a062	journal	October 1964
The Synthesis of Furan, Thiophene, and Pyrrole-3,4-Dicarboxylic Esters Kornfeld, E. C.; Jones, R. G. The Journal of Organic Chemistry, Vol. 19, Issue 10 https://doi.org/10.1021/jo01375a017	journal	October 1954
Clathrate-Formation Mediated Adsorption of Methane on Cu-Complex Crystals Noguchi, Hiroshi; Kondoh, Atsushi; Hattori, Yoshiyuki The Journal of Physical Chemistry B, Vol. 109, Issue 29 https://doi.org/10.1021/jp052515o	journal	July 2005
Temperature Induced Structural Transformations and Gas Adsorption in the Zeolitic Imidazolate Framework ZIF-8: A Raman Study Kumari, Gayatri; Jayaramulu, Kolleboyina; Maji, Tapas Kumar The Journal of Physical Chemistry A, Vol. 117, Issue 43 https://doi.org/10.1021/jp407792a	journal	October 2013
Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry Ye, Chengfeng; Gard, Gary L.; Winter, Rolf W. Organic Letters, Vol. 9, Issue 19 https://doi.org/10.1021/ol701602a	journal	September 2007
Methane storage in flexible metal–organic frameworks with intrinsic thermal management Mason, Jarad A.; Oktawiec, Julia; Taylor, Mercedes K. Nature, Vol. 527, Issue 7578 https://doi.org/10.1038/nature15732	journal	October 2015
Tuning the balance between dispersion and entropy to design temperature-responsive flexible metal-organic frameworks Wieme, J.; Lejaeghere, K.; Kresse, G. Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-07298-4	journal	November 2018
Deacylative transformations of ketones via aromatization-promoted C–C bond activation Xu, Yan; Qi, Xiaotian; Zheng, Pengfei Nature, Vol. 567, Issue 7748 https://doi.org/10.1038/s41586-019-0926-8	journal	January 2019
Fe/Ga-CFA-6 – metal organic frameworks featuring trivalent metal centers and the 4,4′-bipyrazolyl ligand Spirkl, Sebastian; Grzywa, Maciej; Zehe, Christoph S. CrystEngComm, Vol. 17, Issue 2 https://doi.org/10.1039/C4CE01583E	journal	January 2015
Review: biologically active pyrazole derivatives Ansari, Anam; Ali, Abad; Asif, Mohd New Journal of Chemistry, Vol. 41, Issue 1 https://doi.org/10.1039/C6NJ03181A	journal	January 2017
Hysteretic Adsorption and Desorption of Hydrogen by Nanoporous Metal-Organic Frameworks Zhao, X. Science, Vol. 306, Issue 5698 https://doi.org/10.1126/science.1101982	journal	November 2004
Separation of Hexane Isomers in a Metal-Organic Framework with Triangular Channels Herm, Z. R.; Wiers, B. M.; Mason, J. A. Science, Vol. 340, Issue 6135, p. 960-964 https://doi.org/10.1126/science.1234071	journal	May 2013
Synthetic reactions of dimethylformamide. XV. Synthesis of symmetrical tetraformylethane Arnold, Z. Collection of Czechoslovak Chemical Communications, Vol. 27, Issue 12 https://doi.org/10.1135/cccc19622993	journal	January 1962

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