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

doi:10.1039/C9CC08614E

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

Abstract

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

Authors:

^[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

Publication Date:: 2020-01-28

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

OSTI Identifier:: 1581029

Grant/Contract Number:: AC02-06CH11357; AC02-05CH11231; NA-0003525

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: ChemComm

Additional Journal Information:: Journal Name: ChemComm Journal Volume: 56 Journal Issue: 8; Journal ID: ISSN 1359-7345

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Taylor, Mercedes K., Juhl, Martin, Hadaf, Gul Barg, Hwang, Dasol, Velasquez, Ever, Oktawiec, Julia, Lefton, Jonathan B., Runčevski, Tomče, Long, Jeffrey R., and Lee, Ji-Woong. Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate).  United Kingdom: N. p., 2020. 
        Web.  doi:10.1039/C9CC08614E.

Copy to clipboard


                    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. Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate).  United Kingdom.  doi:10.1039/C9CC08614E.

Copy to clipboard


                    Taylor, Mercedes K., Juhl, Martin, Hadaf, Gul Barg, Hwang, Dasol, Velasquez, Ever, Oktawiec, Julia, Lefton, Jonathan B., Runčevski, Tomče, Long, Jeffrey R., and Lee, Ji-Woong. Tue .  
        "Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)".  United Kingdom.  doi:10.1039/C9CC08614E.

Copy to clipboard


                    
@article{osti_1581029,

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

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

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

  doi          = {10.1039/C9CC08614E},

  journal      = {ChemComm},

  number       = 8,

  volume       = 56,

  place        = {United Kingdom},

  year         = {2020},

  month        = {1}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (Publisher)

Publisher's Version of Record
DOI: 10.1039/C9CC08614E

Other availability

Search WorldCat to find libraries that may hold this journal

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction
journal, December 2016

Jedinák, Lukáš; Zátopková, Renáta; Zemánková, Hana
The Journal of Organic Chemistry, Vol. 82, Issue 1
DOI: 10.1021/acs.joc.6b02306

Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry
journal, September 2007

Ye, Chengfeng; Gard, Gary L.; Winter, Rolf W.
Organic Letters, Vol. 9, Issue 19
DOI: 10.1021/ol701602a

The Synthesis of Furan, Thiophene, and Pyrrole-3,4-Dicarboxylic Esters
journal, October 1954

Kornfeld, E. C.; Jones, R. G.
The Journal of Organic Chemistry, Vol. 19, Issue 10
DOI: 10.1021/jo01375a017

Review: biologically active pyrazole derivatives
journal, January 2017

Ansari, Anam; Ali, Abad; Asif, Mohd
New Journal of Chemistry, Vol. 41, Issue 1
DOI: 10.1039/C6NJ03181A

Synthetic reactions of dimethylformamide. XV. Synthesis of symmetrical tetraformylethane
journal, January 1962

Arnold, Z.
Collection of Czechoslovak Chemical Communications, Vol. 27, Issue 12
DOI: 10.1135/cccc19622993

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
journal, September 2017

Spirkl, Sebastian; Grzywa, Maciej; Reschke, Stephan
Inorganic Chemistry, Vol. 56, Issue 20
DOI: 10.1021/acs.inorgchem.7b01818

Tuning the balance between dispersion and entropy to design temperature-responsive flexible metal-organic frameworks
journal, November 2018

Wieme, J.; Lejaeghere, K.; Kresse, G.
Nature Communications, Vol. 9, Issue 1
DOI: 10.1038/s41467-018-07298-4

Coordination chemistry of pyrazole-derived ligands
journal, October 1972

Trofimenko, Swiatoslaw.
Chemical Reviews, Vol. 72, Issue 5
DOI: 10.1021/cr60279a003

1,1,2,2-Ethanetetracarboxaldehyde and Its Reactions
journal, October 1964

Trofimenko, S.
The Journal of Organic Chemistry, Vol. 29, Issue 10
DOI: 10.1021/jo01033a062

Complex Adsorption of Short Linear Alkanes in the Flexible Metal-Organic-Framework MIL-53(Fe)
journal, September 2009

Llewellyn, P. L.; Horcajada, P.; Maurin, G.
Journal of the American Chemical Society, Vol. 131, Issue 36
DOI: 10.1021/ja902740r

Raman and IR Studies of Pressure- and Temperature-Induced Phase Transitions in [(CH 2 ) 3 NH 2 ][Zn(HCOO) 3 ]
journal, November 2014

Mączka, Mirosław; da Silva, Tercio Almeida; Paraguassu, Waldeci
Inorganic Chemistry, Vol. 53, Issue 23
DOI: 10.1021/ic502426x

Tuning the Adsorption Properties of Isoreticular Pyrazolate-Based Metal–Organic Frameworks through Ligand Modification
journal, July 2012

Colombo, Valentina; Montoro, Carmen; Maspero, Angelo
Journal of the American Chemical Society, Vol. 134, Issue 30
DOI: 10.1021/ja305267m

Tuning the Adsorption-Induced Phase Change in the Flexible Metal–Organic Framework Co(bdp)
journal, November 2016

Taylor, Mercedes K.; Runčevski, Tomče; Oktawiec, Julia
Journal of the American Chemical Society, Vol. 138, Issue 45
DOI: 10.1021/jacs.6b09155

Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction
journal, May 2002

Hassan, Jwanro; Sévignon, Marc; Gozzi, Christel
Chemical Reviews, Vol. 102, Issue 5, p. 1359-1470
DOI: 10.1021/cr000664r

Temperature Induced Structural Transformations and Gas Adsorption in the Zeolitic Imidazolate Framework ZIF-8: A Raman Study
journal, October 2013

Kumari, Gayatri; Jayaramulu, Kolleboyina; Maji, Tapas Kumar
The Journal of Physical Chemistry A, Vol. 117, Issue 43
DOI: 10.1021/jp407792a

Deacylative transformations of ketones via aromatization-promoted C–C bond activation
journal, January 2019

Xu, Yan; Qi, Xiaotian; Zheng, Pengfei
Nature, Vol. 567, Issue 7748
DOI: 10.1038/s41586-019-0926-8

Coordination polymers and metal–organic frameworks based on poly(pyrazole)-containing ligands
journal, January 2016

Pettinari, Claudio; Tăbăcaru, Aurel; Galli, Simona
Coordination Chemistry Reviews, Vol. 307
DOI: 10.1016/j.ccr.2015.08.005

Clathrate-Formation Mediated Adsorption of Methane on Cu-Complex Crystals
journal, July 2005

Noguchi, Hiroshi; Kondoh, Atsushi; Hattori, Yoshiyuki
The Journal of Physical Chemistry B, Vol. 109, Issue 29
DOI: 10.1021/jp052515o

From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles
journal, November 2011

Fustero, Santos; Sánchez-Roselló, María; Barrio, Pablo
Chemical Reviews, Vol. 111, Issue 11
DOI: 10.1021/cr2000459

Metal–Organic Frameworks for Separations
journal, September 2011

Li, Jian-Rong; Sculley, Julian; Zhou, Hong-Cai
Chemical Reviews, Vol. 112, Issue 2, p. 869-932
DOI: 10.1021/cr200190s

Separation of Hexane Isomers in a Metal-Organic Framework with Triangular Channels
journal, May 2013

Herm, Z. R.; Wiers, B. M.; Mason, J. A.
Science, Vol. 340, Issue 6135, p. 960-964
DOI: 10.1126/science.1234071

Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N -Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles
journal, April 2019

Yi, Fanhua; Zhao, Wanjun; Wang, Zikun
Organic Letters, Vol. 21, Issue 9
DOI: 10.1021/acs.orglett.9b00860

The therapeutic voyage of pyrazole and its analogs: A review
journal, September 2016

Khan, Mohemmed Faraz; Alam, Mohammad Mumtaz; Verma, Garima
European Journal of Medicinal Chemistry, Vol. 120
DOI: 10.1016/j.ejmech.2016.04.077

Near-Perfect CO 2 /CH 4 Selectivity Achieved through Reversible Guest Templating in the Flexible Metal–Organic Framework Co(bdp)
journal, July 2018

Taylor, Mercedes K.; Runčevski, Tomče; Oktawiec, Julia
Journal of the American Chemical Society, Vol. 140, Issue 32
DOI: 10.1021/jacs.8b06062

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles
journal, February 2019

Tu, Kim N.; Kim, Scott; Blum, Suzanne A.
Organic Letters, Vol. 21, Issue 5
DOI: 10.1021/acs.orglett.8b04038

Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium
journal, June 2008

Lee, Kooyeon; Lee, Phil Ho
Tetrahedron Letters, Vol. 49, Issue 27
DOI: 10.1016/j.tetlet.2008.04.123

Synthesis of N -Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives
journal, April 2019

Onodera, Shunsuke; Kochi, Takuya; Kakiuchi, Fumitoshi
The Journal of Organic Chemistry, Vol. 84, Issue 10
DOI: 10.1021/acs.joc.9b00673

Methane storage in flexible metal–organic frameworks with intrinsic thermal management
journal, October 2015

Mason, Jarad A.; Oktawiec, Julia; Taylor, Mercedes K.
Nature, Vol. 527, Issue 7578
DOI: 10.1038/nature15732

Influence of Metal Substitution on the Pressure-Induced Phase Change in Flexible Zeolitic Imidazolate Frameworks
journal, November 2018

McGuirk, C. Michael; Runčevski, Tomče; Oktawiec, Julia
Journal of the American Chemical Society, Vol. 140, Issue 46
DOI: 10.1021/jacs.8b09631

Broadly Hysteretic H ₂ Adsorption in the Microporous Metal−Organic Framework Co(1,4-benzenedipyrazolate)
journal, June 2008

Choi, Hye Jin; Dincă, Mircea; Long, Jeffrey R.
Journal of the American Chemical Society, Vol. 130, Issue 25
DOI: 10.1021/ja8024092

Hysteretic Adsorption and Desorption of Hydrogen by Nanoporous Metal-Organic Frameworks
journal, November 2004

Zhao, X.
Science, Vol. 306, Issue 5698
DOI: 10.1126/science.1101982

Thermodynamics of Guest-Induced Structural Transitions in Hybrid Organic−Inorganic Frameworks
journal, October 2008

Coudert, François-Xavier; Jeffroy, Marie; Fuchs, Alain H.
Journal of the American Chemical Society, Vol. 130, Issue 43
DOI: 10.1021/ja805129c

Porous Coordination-Polymer Crystals with Gated Channels Specific for Supercritical Gases
journal, January 2003

Kitaura, Ryo; Seki, Kenji; Akiyama, George
Angewandte Chemie International Edition, Vol. 42, Issue 4
DOI: 10.1002/anie.200390130

Fe/Ga-CFA-6 – metal organic frameworks featuring trivalent metal centers and the 4,4′-bipyrazolyl ligand
journal, January 2015

Spirkl, Sebastian; Grzywa, Maciej; Zehe, Christoph S.
CrystEngComm, Vol. 17, Issue 2
DOI: 10.1039/C4CE01583E

Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety
journal, September 2016

Taydakov, Ilya V.; Akkuzina, Alina A.; Avetisov, Roman I.
Journal of Luminescence, Vol. 177
DOI: 10.1016/j.jlumin.2016.04.017

4,4′-Bipyrazolyl: new bitopic connector for construction of coordination networks
journal, October 2002

Boldog, Ishtvan; Sieler, Joachim; Chernega, Alexander N.
Inorganica Chimica Acta, Vol. 338
DOI: 10.1016/S0020-1693(02)00902-7

Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids: Key Involvement of a Palladium Peroxo Complex
journal, May 2006

Adamo, Carlo; Amatore, Christian; Ciofini, Ilaria
Journal of the American Chemical Society, Vol. 128, Issue 21
DOI: 10.1021/ja0569959

N-Dealkylation of pyrazoles using pyridine hydrochloride
journal, May 1975

Butler, Donald E.; DeWald, Horace A.
The Journal of Organic Chemistry, Vol. 40, Issue 9
DOI: 10.1021/jo00897a041

3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1
journal, August 2015

Pelcman, Benjamin; Sanin, Andrei; Nilsson, Peter
Bioorganic & Medicinal Chemistry Letters, Vol. 25, Issue 15
DOI: 10.1016/j.bmcl.2015.05.004

Novel Coordination Frameworks Incorporating the 4,4′-Bipyrazolyl Ditopic Ligand
journal, April 2012

Pettinari, Claudio; Tăbăcaru, Aurel; Boldog, Ishtvan
Inorganic Chemistry, Vol. 51, Issue 9
DOI: 10.1021/ic3001416

Tetrahedral Zinc Complexes with Liquid Crystalline and Luminescent Properties: Interplay Between Nonconventional Molecular Shapes and Supramolecular Mesomorphic Order
journal, September 2007

Cavero, Emma; Uriel, Santiago; Romero, Pilar
Journal of the American Chemical Society, Vol. 129, Issue 37
DOI: 10.1021/ja073639c

Photophysical and Electrochemical Properties of Heteroleptic Tris-Cyclometalated Iridium(III) Complexes
journal, June 2005

Dedeian, Kenneth; Shi, Jianmin; Shepherd, Nigel
Inorganic Chemistry, Vol. 44, Issue 13
DOI: 10.1021/ic050324u

Similar Records in DOE PAGES and OSTI.GOV collections:

Pd-Catalyzed Homocoupling of Pyrazole Boronic Esters to Access Bipyrazoles for Metal-Organic Frameworks.

Conference Taylor, Mercedes ; Juhl, Martin ; Hadaf, Gul Barg ; ...

Abstract not provided.
Full Text Available
Homocoupling Reactions of Azoles and Their Applications in Coordination Chemistry

Journal Article Mogensen, Steffen B. ; Taylor, Mercedes K. ; Lee, Ji-Woong - Molecules

Pyrazole, a member of the structural class of azoles, exhibits molecular properties of interest in pharmaceuticals and materials chemistry, owing to the two adjacent nitrogen atoms in the five-membered ring system. The weakly basic nitrogen atoms of deprotonated pyrazoles have been applied in coordination chemistry, particularly to access coordination polymers and metal-organic frameworks, and homocoupling reactions can in principle provide facile access to bipyrazole ligands. In this context, we summarize recent advances in homocoupling reactions of pyrazoles and other types of azoles (imidazoles, triazoles and tetrazoles) to highlight the utility of homocoupling reactions in synthesizing symmetric bi-heteroaryl systems compared withmore »« less
DOI: 10.3390/molecules25245950

Full Text Available
Aryl mesylates in metal-catalyzed homocoupling and cross-coupling reactions. 1. Functional symmetrical biaryls from phenols via nickel-catalyzed homocoupling of their mesylates

Journal Article Percec, V ; Bae, Jin-Young ; Zhao, Mingyang ; ... - Journal of Organic Chemistry

Aryl sulfonates including derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2{prime}-, 3,3{prime}-, and 4,4{prime}-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on themore »« less
DOI: 10.1021/jo00106a031
Palladium-catalyzed stereospecific homocoupling of vinylstannanes as a suitable method for the synthesis of symmetrical 1,3-dienes

Journal Article Tolstikov, G A ; Miftakhov, M S ; Danilova, N A ; ... - J. Org. Chem. USSR (Engl. Transl.); (United States)

The authors have found that functionally substituted vinylstannanes readily enter into a homocoupling reaction in the presence of 5 mole % of PdCl/sub 2/(MeCN)/sub 2/ (in HMPTA at 20/degree/C), giving 85-95% yields of symmetrical 1,3-dienes with retention of the configuration of the substituents at the double bonds. It should be noted that the rate of this reaction is determined by the configuration of the isomers with respect to the double bond and by the structure of the substituent at the double bond.
A two-fold interpenetrating 3D metal-organic framework material constructed from helical chains linked via 4,4'-H{sub 2}bpz fragments

Journal Article Yiming, Xie ; College of Materials Science and Engineering, Huaqiao University, the Key Laboratory for Functional Materials of Fujian Higher Education, Quanzhou, Fujian 362021 ; Zhenguo, Zhao ; ... - Journal of Solid State Chemistry

A 3-connected dia-f-type metal-organic framework compound {l_brace}[Ag(L){sub 3/2}H{sub 2}PO{sub 4}]{r_brace}{sub n} (1) has been synthesized by self-assembly of 4,4'-H{sub 2}bpz (L=4,4'-H{sub 2}bpz=3,3',5,5'-tetramethyl-4,4'-bipyrazole) and Ag{sub 4}P{sub 2}O{sub 7} under hydrothermal conditions. It crystallizes in the tetragonal space group I4{sub 1}/acd with a=21.406(4) A, b=21.406(4) A, c=36.298(8) A, Z=32. X-ray single-crystal diffraction reveals that 1 has a three-dimensional framework with an unprecedented alternate left- and right-handed helices structure, featuring a non-uniform two-fold interpenetrated (4.14{sup 2}) net. Photoluminescent investigation reveals that the title compound displays interesting emissions in a wide region, which shows that the title compound may be a good potential candidatemore »« less

Similar Records

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

Abstract

Citation Formats

The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction journal, December 2016

Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry journal, September 2007

The Synthesis of Furan, Thiophene, and Pyrrole-3,4-Dicarboxylic Esters journal, October 1954

Review: biologically active pyrazole derivatives journal, January 2017

Synthetic reactions of dimethylformamide. XV. Synthesis of symmetrical tetraformylethane journal, January 1962

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 journal, September 2017

Tuning the balance between dispersion and entropy to design temperature-responsive flexible metal-organic frameworks journal, November 2018

Coordination chemistry of pyrazole-derived ligands journal, October 1972

1,1,2,2-Ethanetetracarboxaldehyde and Its Reactions journal, October 1964

Complex Adsorption of Short Linear Alkanes in the Flexible Metal-Organic-Framework MIL-53(Fe) journal, September 2009

Raman and IR Studies of Pressure- and Temperature-Induced Phase Transitions in [(CH 2 ) 3 NH 2 ][Zn(HCOO) 3 ] journal, November 2014

Tuning the Adsorption Properties of Isoreticular Pyrazolate-Based Metal–Organic Frameworks through Ligand Modification journal, July 2012

Tuning the Adsorption-Induced Phase Change in the Flexible Metal–Organic Framework Co(bdp) journal, November 2016

Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction journal, May 2002

Temperature Induced Structural Transformations and Gas Adsorption in the Zeolitic Imidazolate Framework ZIF-8: A Raman Study journal, October 2013

Deacylative transformations of ketones via aromatization-promoted C–C bond activation journal, January 2019

Coordination polymers and metal–organic frameworks based on poly(pyrazole)-containing ligands journal, January 2016

Clathrate-Formation Mediated Adsorption of Methane on Cu-Complex Crystals journal, July 2005

From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles journal, November 2011

Metal–Organic Frameworks for Separations journal, September 2011

Separation of Hexane Isomers in a Metal-Organic Framework with Triangular Channels journal, May 2013

Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N -Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles journal, April 2019

The therapeutic voyage of pyrazole and its analogs: A review journal, September 2016

Near-Perfect CO 2 /CH 4 Selectivity Achieved through Reversible Guest Templating in the Flexible Metal–Organic Framework Co(bdp) journal, July 2018

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles journal, February 2019

Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium journal, June 2008

Synthesis of N -Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives journal, April 2019

Methane storage in flexible metal–organic frameworks with intrinsic thermal management journal, October 2015

Influence of Metal Substitution on the Pressure-Induced Phase Change in Flexible Zeolitic Imidazolate Frameworks journal, November 2018

Broadly Hysteretic H 2 Adsorption in the Microporous Metal−Organic Framework Co(1,4-benzenedipyrazolate) journal, June 2008

Hysteretic Adsorption and Desorption of Hydrogen by Nanoporous Metal-Organic Frameworks journal, November 2004

Thermodynamics of Guest-Induced Structural Transitions in Hybrid Organic−Inorganic Frameworks journal, October 2008

Porous Coordination-Polymer Crystals with Gated Channels Specific for Supercritical Gases journal, January 2003

Fe/Ga-CFA-6 – metal organic frameworks featuring trivalent metal centers and the 4,4′-bipyrazolyl ligand journal, January 2015

Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety journal, September 2016

4,4′-Bipyrazolyl: new bitopic connector for construction of coordination networks journal, October 2002

Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids: Key Involvement of a Palladium Peroxo Complex journal, May 2006

N-Dealkylation of pyrazoles using pyridine hydrochloride journal, May 1975

3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1 journal, August 2015

Novel Coordination Frameworks Incorporating the 4,4′-Bipyrazolyl Ditopic Ligand journal, April 2012

Tetrahedral Zinc Complexes with Liquid Crystalline and Luminescent Properties: Interplay Between Nonconventional Molecular Shapes and Supramolecular Mesomorphic Order journal, September 2007

Photophysical and Electrochemical Properties of Heteroleptic Tris-Cyclometalated Iridium(III) Complexes journal, June 2005

The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction
journal, December 2016

Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry
journal, September 2007

The Synthesis of Furan, Thiophene, and Pyrrole-3,4-Dicarboxylic Esters
journal, October 1954

Review: biologically active pyrazole derivatives
journal, January 2017

Synthetic reactions of dimethylformamide. XV. Synthesis of symmetrical tetraformylethane
journal, January 1962

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
journal, September 2017

Tuning the balance between dispersion and entropy to design temperature-responsive flexible metal-organic frameworks
journal, November 2018

Coordination chemistry of pyrazole-derived ligands
journal, October 1972

1,1,2,2-Ethanetetracarboxaldehyde and Its Reactions
journal, October 1964

Complex Adsorption of Short Linear Alkanes in the Flexible Metal-Organic-Framework MIL-53(Fe)
journal, September 2009

Raman and IR Studies of Pressure- and Temperature-Induced Phase Transitions in [(CH 2 ) 3 NH 2 ][Zn(HCOO) 3 ]
journal, November 2014

Tuning the Adsorption Properties of Isoreticular Pyrazolate-Based Metal–Organic Frameworks through Ligand Modification
journal, July 2012

Tuning the Adsorption-Induced Phase Change in the Flexible Metal–Organic Framework Co(bdp)
journal, November 2016

Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction
journal, May 2002

Temperature Induced Structural Transformations and Gas Adsorption in the Zeolitic Imidazolate Framework ZIF-8: A Raman Study
journal, October 2013

Deacylative transformations of ketones via aromatization-promoted C–C bond activation
journal, January 2019

Coordination polymers and metal–organic frameworks based on poly(pyrazole)-containing ligands
journal, January 2016

Clathrate-Formation Mediated Adsorption of Methane on Cu-Complex Crystals
journal, July 2005

From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles
journal, November 2011

Metal–Organic Frameworks for Separations
journal, September 2011

Separation of Hexane Isomers in a Metal-Organic Framework with Triangular Channels
journal, May 2013

Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N -Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles
journal, April 2019

The therapeutic voyage of pyrazole and its analogs: A review
journal, September 2016

Near-Perfect CO 2 /CH 4 Selectivity Achieved through Reversible Guest Templating in the Flexible Metal–Organic Framework Co(bdp)
journal, July 2018

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles
journal, February 2019

Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium
journal, June 2008

Synthesis of N -Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives
journal, April 2019

Methane storage in flexible metal–organic frameworks with intrinsic thermal management
journal, October 2015

Influence of Metal Substitution on the Pressure-Induced Phase Change in Flexible Zeolitic Imidazolate Frameworks
journal, November 2018

Broadly Hysteretic H ₂ Adsorption in the Microporous Metal−Organic Framework Co(1,4-benzenedipyrazolate)
journal, June 2008

Hysteretic Adsorption and Desorption of Hydrogen by Nanoporous Metal-Organic Frameworks
journal, November 2004

Thermodynamics of Guest-Induced Structural Transitions in Hybrid Organic−Inorganic Frameworks
journal, October 2008

Porous Coordination-Polymer Crystals with Gated Channels Specific for Supercritical Gases
journal, January 2003

Fe/Ga-CFA-6 – metal organic frameworks featuring trivalent metal centers and the 4,4′-bipyrazolyl ligand
journal, January 2015

Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety
journal, September 2016

4,4′-Bipyrazolyl: new bitopic connector for construction of coordination networks
journal, October 2002

Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids: Key Involvement of a Palladium Peroxo Complex
journal, May 2006

N-Dealkylation of pyrazoles using pyridine hydrochloride
journal, May 1975

3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1
journal, August 2015

Novel Coordination Frameworks Incorporating the 4,4′-Bipyrazolyl Ditopic Ligand
journal, April 2012

Tetrahedral Zinc Complexes with Liquid Crystalline and Luminescent Properties: Interplay Between Nonconventional Molecular Shapes and Supramolecular Mesomorphic Order
journal, September 2007

Photophysical and Electrochemical Properties of Heteroleptic Tris-Cyclometalated Iridium(III) Complexes
journal, June 2005