A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones

Heintz, Patrick M.; Schumacher, Brian P.; Chen, Minda; Huang, Wenyu; Stanley, Levi M.

doi:10.1002/cctc.201900894

Title: A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones

Abstract

A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) built from 1,3,5-triformylphloroglucinol (Tp) and [2,2'-bipyridine]-5,5'-diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions of an array of stereoelectronically diverse arylboronic acid nucleophiles to β,β-disubstituted enones form a variety of ketones containing benzylic all-carbon quaternary centers in up to 92 % isolated yield. Research on the recyclability of Pd@TpBpy COF demonstrate this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.

Authors:

Heintz, Patrick M. ^[1]; Schumacher, Brian P. ^[2]; Chen, Minda ^[1]; Huang, Wenyu ^[1];

^[2]

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

Publication Date:: 2019-06-25

Research Org.:: Ames Lab., Ames, IA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1557818

Alternate Identifier(s):: OSTI ID: 1547943

Report Number(s):: IS-J-10004
Journal ID: ISSN 1867-3880

Grant/Contract Number:: AC02-07CH11358

Resource Type:: Accepted Manuscript

Journal Name:: ChemCatChem

Additional Journal Information:: Journal Volume: 11; Journal Issue: 17; Journal ID: ISSN 1867-3880

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; covalent organic framework (COF); conjugate addition; palladium; quaternary centers; heterogeneous catalysis

Citation Formats


                    Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, and Stanley, Levi M. A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones.  United States: N. p., 2019. 
Web.  doi:10.1002/cctc.201900894.

Copy to clipboard


                    Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, & Stanley, Levi M. A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones.  United States.  https://doi.org/10.1002/cctc.201900894

Copy to clipboard


                    Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, and Stanley, Levi M. Tue .  
"A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones".  United States.  https://doi.org/10.1002/cctc.201900894.  https://www.osti.gov/servlets/purl/1557818.

Copy to clipboard


                    
@article{osti_1557818,

  title        = {A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones},

  author       = {Heintz, Patrick M. and Schumacher, Brian P. and Chen, Minda and Huang, Wenyu and Stanley, Levi M.},

  abstractNote = {A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) built from 1,3,5-triformylphloroglucinol (Tp) and [2,2'-bipyridine]-5,5'-diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions of an array of stereoelectronically diverse arylboronic acid nucleophiles to β,β-disubstituted enones form a variety of ketones containing benzylic all-carbon quaternary centers in up to 92 % isolated yield. Research on the recyclability of Pd@TpBpy COF demonstrate this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.},

  doi          = {10.1002/cctc.201900894},

  journal      = {ChemCatChem},

  number       = 17,

  volume       = 11,

  place        = {United States},

  year         = {2019},

  month        = {6}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (Publisher)

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1002/cctc.201900894

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:

Salen-Based Covalent Organic Framework
journal, April 2017

Li, Li-Hua; Feng, Xiao-Lin; Cui, Xiao-Hui
Journal of the American Chemical Society, Vol. 139, Issue 17
DOI: 10.1021/jacs.7b01523

Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
journal, September 2016

Wang, Xiuren; Han, Xing; Zhang, Jie
Journal of the American Chemical Society, Vol. 138, Issue 38
DOI: 10.1021/jacs.6b07714

Constructing Crystalline Covalent Organic Frameworks from Chiral Building Blocks
journal, September 2016

Xu, Hai-Sen; Ding, San-Yuan; An, Wan-Kai
Journal of the American Chemical Society, Vol. 138, Issue 36
DOI: 10.1021/jacs.6b07516

Chemistry of Covalent Organic Frameworks
journal, November 2015

Waller, Peter J.; Gándara, Felipe; Yaghi, Omar M.
Accounts of Chemical Research, Vol. 48, Issue 12
DOI: 10.1021/acs.accounts.5b00369

Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route
journal, November 2012

Kandambeth, Sharath; Mallick, Arijit; Lukose, Binit
Journal of the American Chemical Society, Vol. 134, Issue 48
DOI: 10.1021/ja308278w

Covalent organic frameworks (COFs): perspectives of industrialization
journal, January 2018

Zhao, Wei; Xia, Lieyin; Liu, Xikui
CrystEngComm, Vol. 20, Issue 12
DOI: 10.1039/C7CE02079A

Covalent organic frameworks (COFs): from design to applications
journal, January 2013

Ding, San-Yuan; Wang, Wei
Chem. Soc. Rev., Vol. 42, Issue 2
DOI: 10.1039/C2CS35072F

A tunable azine covalent organic framework platform for visible light-induced hydrogen generation
journal, September 2015

Vyas, Vijay S.; Haase, Frederik; Stegbauer, Linus
Nature Communications, Vol. 6, Issue 1
DOI: 10.1038/ncomms9508

Highly Stable Keto-Enamine Salicylideneanilines
journal, October 2003

Chong, Jonathan H.; Sauer, Marc; Patrick, Brian O.
Organic Letters, Vol. 5, Issue 21
DOI: 10.1021/ol0352714

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho -Substituted Benzylic Quaternary Centers
journal, August 2015

Van Zeeland, Ryan; Stanley, Levi M.
ACS Catalysis, Vol. 5, Issue 9
DOI: 10.1021/acscatal.5b01272

Pd loaded amphiphilic COF as catalyst for multi-fold Heck reactions, C-C couplings and CO oxidation
journal, June 2015

Mullangi, Dinesh; Nandi, Shyamapada; Shalini, Sorout
Scientific Reports, Vol. 5, Issue 1
DOI: 10.1038/srep10876

Three-dimensional Salphen-based Covalent–Organic Frameworks as Catalytic Antioxidants
journal, February 2019

Yan, Shichen; Guan, Xinyu; Li, Hui
Journal of the American Chemical Society, Vol. 141, Issue 7
DOI: 10.1021/jacs.9b00485

Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki–Miyaura Coupling Reaction
journal, December 2011

Ding, San-Yuan; Gao, Jia; Wang, Qiong
Journal of the American Chemical Society, Vol. 133, Issue 49
DOI: 10.1021/ja206846p

Covalent organic frameworks: a materials platform for structural and functional designs
journal, September 2016

Huang, Ning; Wang, Ping; Jiang, Donglin
Nature Reviews Materials, Vol. 1, Issue 10
DOI: 10.1038/natrevmats.2016.68

Covalent Triazine Frameworks as Heterogeneous Catalysts for the Synthesis of Cyclic and Linear Carbonates from Carbon Dioxide and Epoxides
journal, August 2012

Roeser, Jérôme; Kailasam, Kamalakannan; Thomas, Arne
ChemSusChem, Vol. 5, Issue 9
DOI: 10.1002/cssc.201200091

Heterogeneous Catalysis by Covalent Organic Frameworks (COF): Pd(OAc) ₂ @COF-300 in Cross-Coupling Reactions
journal, January 2016

Gonçalves, Raoni S. B.; de Oliveira, Alline B. V.; Sindra, Haryadylla C.
ChemCatChem, Vol. 8, Issue 4
DOI: 10.1002/cctc.201500926

Stable Covalent Organic Frameworks as Efficient Adsorbents for High and Selective Removal of an Aryl-Organophosphorus Flame Retardant from Water
journal, August 2018

Wang, Wei; Deng, Shubo; Ren, Lu
ACS Applied Materials & Interfaces, Vol. 10, Issue 36
DOI: 10.1021/acsami.8b06229

Constructing Ultraporous Covalent Organic Frameworks in Seconds via an Organic Terracotta Process
journal, January 2017

Karak, Suvendu; Kandambeth, Sharath; Biswal, Bishnu P.
Journal of the American Chemical Society, Vol. 139, Issue 5
DOI: 10.1021/jacs.6b08815

A mechanochemically synthesized covalent organic framework as a proton-conducting solid electrolyte
journal, January 2016

Shinde, Digambar Balaji; Aiyappa, Harshitha Barike; Bhadra, Mohitosh
Journal of Materials Chemistry A, Vol. 4, Issue 7
DOI: 10.1039/C5TA10521H

5,5′-Diamino-2,2′-bipyridine: A Versatile Building Block for the Synthesis of Bipyridine/Catechol Ligands That Form Homo- and Heteronuclear Helicates
journal, September 2005

Albrecht, Markus; Janser, Ingo; Lützen, Arne
Chemistry - A European Journal, Vol. 11, Issue 19
DOI: 10.1002/chem.200401262

Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis
journal, March 2018

Wei, Pi-Feng; Qi, Ming-Zhu; Wang, Zhi-Peng
Journal of the American Chemical Society, Vol. 140, Issue 13
DOI: 10.1021/jacs.8b00571

Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis
journal, June 2017

Han, Xing; Xia, Qingchun; Huang, Jinjing
Journal of the American Chemical Society, Vol. 139, Issue 25
DOI: 10.1021/jacs.7b04008

Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications
journal, January 2016

Segura, José L.; Mancheño, María J.; Zamora, Félix
Chemical Society Reviews, Vol. 45, Issue 20
DOI: 10.1039/C5CS00878F

Cobalt-Modified Covalent Organic Framework as a Robust Water Oxidation Electrocatalyst
journal, June 2016

Aiyappa, Harshitha Barike; Thote, Jayshri; Shinde, Digambar Balaji
Chemistry of Materials, Vol. 28, Issue 12
DOI: 10.1021/acs.chemmater.6b01370

Impact of Linker Engineering on the Catalytic Activity of Metal–Organic Frameworks Containing Pd(II)–Bipyridine Complexes
journal, August 2016

Li, Xinle; Van Zeeland, Ryan; Maligal-Ganesh, Raghu V.
ACS Catalysis, Vol. 6, Issue 9
DOI: 10.1021/acscatal.6b01753

3D Porphyrin-Based Covalent Organic Frameworks
journal, June 2017

Lin, Guiqing; Ding, Huimin; Chen, Rufan
Journal of the American Chemical Society, Vol. 139, Issue 25
DOI: 10.1021/jacs.7b04141

Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts
journal, September 2015

Xu, Hong; Gao, Jia; Jiang, Donglin
Nature Chemistry, Vol. 7, Issue 11
DOI: 10.1038/nchem.2352

Highly Efficient Heterogeneous Hydroformylation over Rh-Metalated Porous Organic Polymers: Synergistic Effect of High Ligand Concentration and Flexible Framework
journal, April 2015

Sun, Qi; Dai, Zhifeng; Liu, Xiaolong
Journal of the American Chemical Society, Vol. 137, Issue 15
DOI: 10.1021/jacs.5b02122

3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery
journal, June 2015

Fang, Qianrong; Wang, Junhua; Gu, Shuang
Journal of the American Chemical Society, Vol. 137, Issue 26
DOI: 10.1021/jacs.5b04147

Covalent organic frameworks comprising cobalt porphyrins for catalytic CO ₂ reduction in water
journal, August 2015

Lin, Song; Diercks, Christian S.; Zhang, Yue-Biao
Science, Vol. 349, Issue 6253
DOI: 10.1126/science.aac8343

Macro/Microporous Covalent Organic Frameworks for Efficient Electrocatalysis
journal, March 2019

Zhao, Xiaojia; Pachfule, Pradip; Li, Shuang
Journal of the American Chemical Society, Vol. 141, Issue 16
DOI: 10.1021/jacs.9b01226

Synthesis of Benzobisoxazole-Linked Two-Dimensional Covalent Organic Frameworks and Their Carbon Dioxide Capture Properties
journal, August 2016

Pyles, David A.; Crowe, Jonathan W.; Baldwin, Luke A.
ACS Macro Letters, Vol. 5, Issue 9
DOI: 10.1021/acsmacrolett.6b00486

Similar Records in DOE PAGES and OSTI.GOV collections:

MOF-253-Pd(OAc)₂ : a recyclable MOF for transition-metal catalysis in water

Journal Article Van Zeeland, Ryan ; Li, Xinle ; Huang, Wenyu ; ... - RSC Advances

We report palladium(II)-functionalized MOF-253 (MOF-253-Pd(OAc)₂) as a recyclable catalyst to form all-carbon quaternary centers via conjugate additions of arylboronic acids to β,β-disubstituted enones in aqueous media. We demonstrate MOF-253-Pd(OAc)₂ can be reused 8 times to form ketone products in yields above 75% while maintaining its crystallinity. Additions of a range of stereoelectronically diverse arylboronic acids to a variety of β,β-disubstituted enones catalyzed by MOF-253-Pd(OAc)₂ occur in modest-to-high yields (34–95%).
Cited by 4
https://doi.org/10.1039/c6ra12746k

Full Text Available
Photoelectrochemical alcohol oxidation by mixed-linker metal–organic frameworks

Journal Article Lin, Shaoyang ; Cairnie, Daniel R. ; Davis, Dylan ; ... - Faraday Discussions

Metal–organic frameworks (MOFs) provide a suitable platform for stable and efficient heterogeneous photoelectrochemical oxidation catalysis due to their highly ordered structure, large surface area, and synthetic tunability. Herein, a mixed-linker MOF comprising of a photosensitizer [Ru(dcbpy)(bpy)₂]²⁺ (bpy = 2,2'-bipyridine, dcbpy = 5,5'-dicarboxy-2,2'-bipyridine) and catalyst [Ru(tpy)(dcbpy)Cl]⁺ (tpy = 2,2':6',2''-terpyridine) that were incorporated into the UiO-67 framework and grown as thin films on a TiO₂-coated, fluorine-doped tin oxide (FTO) electrode (RuB-RuTB-UiO-67/TiO₂/FTO). When used as an electrode for the photoelectrochemical oxidation of benzyl alcohol, the mixed-linker MOF film showed a faradaic efficiency of 34%, corresponding to a 3-fold increase in efficiency relative tomore »« less
https://doi.org/10.1039/d0fd00021c

Full Text Available
Unveiling the Effects of Linker Substitution in Suzuki Coupling with Palladium Nanoparticles in Metal–Organic Frameworks [Unveiling the Effects of Linker Substitution in Suzuki Coupling Reaction with Palladium Nanoparticles in Metal–Organic Frameworks]

Journal Article Li, Xinle ; Zhang, Biying ; Van Zeeland, Ryan ; ... - Catalysis Letters

The establishment of structure–property relationships in heterogeneous catalysis is of prime importance but remains a formidable challenge. Metal–organic frameworks (MOFs) featuring excellent chemical tunability are emerging as an auspicious platform for the atomic-level control of heterogeneous catalysis. Herein, we encapsulate palladium nanoparticles (Pd NPs) in a series of isoreticular mixed-linker MOFs, and the obtained MOF-Pd NPs catalysts were used to unveil the electronic and steric effects of linker substitution on the activity of these catalysts in the Suzuki–Miyaura cross-coupling reactions. Significantly, m-6,6'-Me2bpy-MOF-Pd exhibits a remarkable enhancement in the activity compared to non-functionalized m-bpy-MOF-Pd and m-4,4'-Me₂bpy-MOF-Pd. This study unambiguously demonstrates thatmore »« less
Cited by 3
https://doi.org/10.1007/s10562-017-2289-9

Full Text Available
Urea-Linked Covalent Organic Frameworks

Journal Article Zhao, Chenfei ; Diercks, Christian S. ; Zhu, Chenhui ; ... - Journal of the American Chemical Society

2D covalent organic frameworks (COFs) with flexible urea linkages have been synthesized by condensation of 1,3,5-triformylphloroglucinol (TFP) with 1,4-phenylenediurea (BDU) or 1,1'-(3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)diurea (DMBDU). The resulting COF-117 and COF-118 undergo reversible structural dynamics within their layers, in response to inclusion and removal of guest molecules, emanating from urea C-N bond rotation and interlayer hydrogen-bonding interactions. Furthermore, these compounds are the first urea-linked COFs, serving to expand the scope of reticular chemistry.
Cited by 26
https://doi.org/10.1021/jacs.8b10612

Full Text Available
Covalent-Organic Frameworks Composed of Rhenium Bipyridine and Metal Porphyrins: Designing Heterobimetallic Frameworks with Two Distinct Metal Sites

Journal Article Johnson, Eric M. ; Haiges, Ralf ; Marinescu, Smaranda C. - ACS Applied Materials and Interfaces

The incorporation of homogeneous catalysts for CO₂ reduction into extended frameworks has been a successful strategy for increasing catalyst lifetime and activity, but the effects of the linkers on catalysis are underexplored. In this work, a novel rhenium bipyridine complex was synthesized for the purpose of designing a covalent-organic framework (COF) with both metalloporphyrin and metal bipyridine moieties. Investigation of the rhenium complex as a homogeneous catalyst shows a faradaic efficiency of 81(8)% for the electrocatalytic conversion of CO₂ to CO upon the addition of methanol as the proton source. Treatment of the rhenium complex with tetra(4-aminophenyl)porphyrin under Schiff basemore »« less
Cited by 27
https://doi.org/10.1021/acsami.8b07795

Full Text Available

Similar Records

Title: A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones

Abstract

Citation Formats

Salen-Based Covalent Organic Framework journal, April 2017

Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis journal, September 2016

Constructing Crystalline Covalent Organic Frameworks from Chiral Building Blocks journal, September 2016

Chemistry of Covalent Organic Frameworks journal, November 2015

Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route journal, November 2012

Covalent organic frameworks (COFs): perspectives of industrialization journal, January 2018

Covalent organic frameworks (COFs): from design to applications journal, January 2013

A tunable azine covalent organic framework platform for visible light-induced hydrogen generation journal, September 2015

Highly Stable Keto-Enamine Salicylideneanilines journal, October 2003

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho -Substituted Benzylic Quaternary Centers journal, August 2015

Pd loaded amphiphilic COF as catalyst for multi-fold Heck reactions, C-C couplings and CO oxidation journal, June 2015

Three-dimensional Salphen-based Covalent–Organic Frameworks as Catalytic Antioxidants journal, February 2019

Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki–Miyaura Coupling Reaction journal, December 2011

Covalent organic frameworks: a materials platform for structural and functional designs journal, September 2016

Covalent Triazine Frameworks as Heterogeneous Catalysts for the Synthesis of Cyclic and Linear Carbonates from Carbon Dioxide and Epoxides journal, August 2012

Heterogeneous Catalysis by Covalent Organic Frameworks (COF): Pd(OAc) 2 @COF-300 in Cross-Coupling Reactions journal, January 2016

Stable Covalent Organic Frameworks as Efficient Adsorbents for High and Selective Removal of an Aryl-Organophosphorus Flame Retardant from Water journal, August 2018

Constructing Ultraporous Covalent Organic Frameworks in Seconds via an Organic Terracotta Process journal, January 2017

A mechanochemically synthesized covalent organic framework as a proton-conducting solid electrolyte journal, January 2016

5,5′-Diamino-2,2′-bipyridine: A Versatile Building Block for the Synthesis of Bipyridine/Catechol Ligands That Form Homo- and Heteronuclear Helicates journal, September 2005

Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis journal, March 2018

Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis journal, June 2017

Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications journal, January 2016

Cobalt-Modified Covalent Organic Framework as a Robust Water Oxidation Electrocatalyst journal, June 2016

Impact of Linker Engineering on the Catalytic Activity of Metal–Organic Frameworks Containing Pd(II)–Bipyridine Complexes journal, August 2016

3D Porphyrin-Based Covalent Organic Frameworks journal, June 2017

Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts journal, September 2015

Highly Efficient Heterogeneous Hydroformylation over Rh-Metalated Porous Organic Polymers: Synergistic Effect of High Ligand Concentration and Flexible Framework journal, April 2015

3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery journal, June 2015

Covalent organic frameworks comprising cobalt porphyrins for catalytic CO 2 reduction in water journal, August 2015

Macro/Microporous Covalent Organic Frameworks for Efficient Electrocatalysis journal, March 2019

Synthesis of Benzobisoxazole-Linked Two-Dimensional Covalent Organic Frameworks and Their Carbon Dioxide Capture Properties journal, August 2016

Salen-Based Covalent Organic Framework
journal, April 2017

Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
journal, September 2016

Constructing Crystalline Covalent Organic Frameworks from Chiral Building Blocks
journal, September 2016

Chemistry of Covalent Organic Frameworks
journal, November 2015

Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route
journal, November 2012

Covalent organic frameworks (COFs): perspectives of industrialization
journal, January 2018

Covalent organic frameworks (COFs): from design to applications
journal, January 2013

A tunable azine covalent organic framework platform for visible light-induced hydrogen generation
journal, September 2015

Highly Stable Keto-Enamine Salicylideneanilines
journal, October 2003

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho -Substituted Benzylic Quaternary Centers
journal, August 2015

Pd loaded amphiphilic COF as catalyst for multi-fold Heck reactions, C-C couplings and CO oxidation
journal, June 2015

Three-dimensional Salphen-based Covalent–Organic Frameworks as Catalytic Antioxidants
journal, February 2019

Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki–Miyaura Coupling Reaction
journal, December 2011

Covalent organic frameworks: a materials platform for structural and functional designs
journal, September 2016

Covalent Triazine Frameworks as Heterogeneous Catalysts for the Synthesis of Cyclic and Linear Carbonates from Carbon Dioxide and Epoxides
journal, August 2012

Heterogeneous Catalysis by Covalent Organic Frameworks (COF): Pd(OAc) ₂ @COF-300 in Cross-Coupling Reactions
journal, January 2016

Stable Covalent Organic Frameworks as Efficient Adsorbents for High and Selective Removal of an Aryl-Organophosphorus Flame Retardant from Water
journal, August 2018

Constructing Ultraporous Covalent Organic Frameworks in Seconds via an Organic Terracotta Process
journal, January 2017

A mechanochemically synthesized covalent organic framework as a proton-conducting solid electrolyte
journal, January 2016

5,5′-Diamino-2,2′-bipyridine: A Versatile Building Block for the Synthesis of Bipyridine/Catechol Ligands That Form Homo- and Heteronuclear Helicates
journal, September 2005

Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis
journal, March 2018

Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis
journal, June 2017

Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications
journal, January 2016

Cobalt-Modified Covalent Organic Framework as a Robust Water Oxidation Electrocatalyst
journal, June 2016

Impact of Linker Engineering on the Catalytic Activity of Metal–Organic Frameworks Containing Pd(II)–Bipyridine Complexes
journal, August 2016

3D Porphyrin-Based Covalent Organic Frameworks
journal, June 2017

Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts
journal, September 2015

Highly Efficient Heterogeneous Hydroformylation over Rh-Metalated Porous Organic Polymers: Synergistic Effect of High Ligand Concentration and Flexible Framework
journal, April 2015

3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery
journal, June 2015

Covalent organic frameworks comprising cobalt porphyrins for catalytic CO ₂ reduction in water
journal, August 2015

Macro/Microporous Covalent Organic Frameworks for Efficient Electrocatalysis
journal, March 2019

Synthesis of Benzobisoxazole-Linked Two-Dimensional Covalent Organic Frameworks and Their Carbon Dioxide Capture Properties
journal, August 2016