Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst

Title: Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst

Abstract

The disclosure provides methods for the use of open metal frameworks to catalyze coupling reactions.

Inventors:: Yaghi, Omar M.; Czaja, Alexander U.; Wang, Bo; Lu, Zheng

Issue Date:: 2015-06-02

Research Org.:: Univ. of California, Oakland, CA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1183458

Patent Number(s):: 9045387

Application Number:: 13/387,598

Assignee:: The Regents of the University of California (Oakland, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C253/30 - by reactions not involving the formation of cyano groups
C07C2523/72 - Copper
C07C25/18 - Polycyclic aromatic halogenated hydrocarbons
C07C255/51 - containing at least two cyano groups bound to the carbon skeleton
C07C15/14 - all phenyl groups being directly linked
C07C201/12 - by reactions not involving the formation of nitro groups
C07C17/263 - by condensation reactions
C07C211/50 - with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
C07C209/68 - from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
C07C1/321 - {the hetero-atom being a non-metal atom}
C07C205/06 - having nitro groups bound to carbon atoms of six-membered aromatic rings
C07C2531/28 - of the platinum group metals, iron group metals or copper

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DOE Contract Number:: FG02-08ER15935

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Yaghi, Omar M., Czaja, Alexander U., Wang, Bo, and Lu, Zheng. Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst.  United States: N. p., 2015. 
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                    Yaghi, Omar M., Czaja, Alexander U., Wang, Bo, & Lu, Zheng. Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst.  United States.

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                    Yaghi, Omar M., Czaja, Alexander U., Wang, Bo, and Lu, Zheng. Tue .  
        "Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst".  United States.  https://www.osti.gov/servlets/purl/1183458.

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@article{osti_1183458,

  title        = {Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst},

  author       = {Yaghi, Omar M. and Czaja, Alexander U. and Wang, Bo and Lu, Zheng},

  abstractNote = {The disclosure provides methods for the use of open metal frameworks to catalyze coupling reactions.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2015},

  month        = {6}

}

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Title: Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst

Abstract

Citation Formats

Implementation of a strategy for achieving extraordinary levels of surface area and porosity in crystals patent, January 2010

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

Palladium-Catalyzed Suzuki-Type Self-Coupling of Arylboronic Acids. A Mechanistic Study journal, January 1996

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

Isoreticular MOFs based on a rhombic dodecahedral MOP as a tertiary building unit journal, January 2014

Post-Synthetic Modification of Tagged Metal-Organic Frameworks journal, October 2008

High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to CO2 Capture journal, February 2008

Control of Pore Size and Functionality in Isoreticular Zeolitic Imidazolate Frameworks and their Carbon Dioxide Selective Capture Properties journal, March 2009

Azulene based metal–organic frameworks for strong adsorption of H2 journal, January 2010

Tailored Porous Materials journal, October 1999

Metal Insertion in a Microporous Metal−Organic Framework Lined with 2,2′-Bipyridine journal, October 2010

1,4-Benzenedicarboxylate derivatives as links in the design of paddle-wheel units and metal–organic frameworks journal, November 2001

Highly efficient separation of carbon dioxide by a metal-organic framework replete with open metal sites journal, November 2009

Ring-Opening Reactions within Porous Metal−Organic Frameworks journal, July 2010

Polycatenation, polythreading and polyknotting in coordination network chemistry journal, November 2003

Dramatic Tuning of Carbon Dioxide Uptake via Metal Substitution in a Coordination Polymer with Cylindrical Pores journal, August 2008

Raman spectra of hydrogen and deuterium adsorbed on a metal–organic framework journal, August 2005

Tertiary Building Units: Synthesis, Structure, and Porosity of a Metal−Organic Dendrimer Framework (MODF-1) October 2001

MOFs as catalysts: Activity, reusability and shape-selectivity of a Pd-containing MOF journal, September 2007

A route to high surface area, porosity and inclusion of large molecules in crystals journal, February 2004

Cu2(ATC)·6H2O: Design of Open Metal Sites in Porous Metal−Organic Crystals (ATC: 1,3,5,7-Adamantane Tetracarboxylate) journal, November 2000

Interwoven Metal-Organic Framework on a Periodic Minimal Surface with Extra-Large Pores journal, February 2001

Transformation of a Metal−Organic Framework from the NbO to PtS Net journal, January 2005

High H2 Adsorption in a Microporous Metal-Organic Framework with Open Metal Sites journal, July 2005

A Microporous Metal–Organic Framework for Gas-Chromatographic Separation of Alkanes journal, February 2006

A metal–organic framework material that functions as an enantioselective catalyst for olefin epoxidation journal, January 2006

Heterogeneity within Order in Crystals of a Porous Metal–Organic Framework journal, August 2011

In Situ Hydrothermal Growth of Metal−Organic Framework 199 Films on Stainless Steel Fibers for Solid-Phase Microextraction of Gaseous Benzene Homologues journal, December 2009

Three-periodic nets and tilings: regular and quasiregular nets journal, December 2002

What do we know about three-periodic nets? journal, August 2005

Three-periodic nets and tilings: edge-transitive binodal structures journal, August 2006

Multiple Functional Groups of Varying Ratios in Metal-Organic Frameworks journal, February 2010

Robust dynamics journal, May 2010

Isoreticular Metalation of Metal−Organic Frameworks journal, July 2009

Design of New Materials for Methane Storage journal, March 2004

Highly Porous and Stable Metal−Organic Frameworks: Structure Design and Sorption Properties journal, February 2000

Porous Metal−Organic Polyhedra: 25 Å Cuboctahedron Constructed from 12 Cu2(CO2)4 Paddle-Wheel Building Blocks journal, May 2001

Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal−Organic Carboxylate Frameworks journal, April 2001

Geometric requirements and examples of important structures in the assembly of square building blocks journal, April 2002

Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage journal, January 2002

Cu2[o-Br-C6H3(CO2)2]2(H2O)2·(DMF)8(H2O)2: A Framework Deliberately Designed To Have the NbO Structure Type journal, January 2002

Positronium formation in porous materials for antihydrogen production journal, April 2010

Independent verification of the saturation hydrogen uptake in MOF-177 and establishment of a benchmark for hydrogen adsorption in metal–organic frameworks journal, January 2007

Control of Vertex Geometry, Structure Dimensionality, Functionality, and Pore Metrics in the Reticular Synthesis of Crystalline Metal−Organic Frameworks and Polyhedra journal, September 2008

Storage of Hydrogen, Methane, and Carbon Dioxide in Highly Porous Covalent Organic Frameworks for Clean Energy Applications journal, July 2009

Ultrahigh Porosity in Metal-Organic Frameworks journal, July 2010

Adsorption of Harmful Organic Vapors by Flexible Hydrophobic Bis-pyrazolate Based MOFs journal, March 2010

MOF-74 building unit has a direct impact on toxic gas adsorption journal, January 2011

Construction of Microporous Materials from Molecular Building Blocks book, January 2002

Construction of Porous Solids from Hydrogen-Bonded Metal Complexes of 1,3,5-Benzenetricarboxylic Acid journal, January 1996

Selective Guest Binding by Tailored Channels in a 3-D Porous Zinc(II)−Benzenetricarboxylate Network journal, March 1997

Crystal Growth of Extended Solids by Nonaqueous Gel Diffusion journal, May 1997

A Molecular Railroad with Large Pores: Synthesis and Structure of Ni(4,4‘-bpy)2.5(H2O)2(ClO4)2·1.5(4,4‘-bpy)·2H2O journal, September 1997

Synthetic Strategies, Structure Patterns, and Emerging Properties in the Chemistry of Modular Porous Solids† journal, August 1998

Design of Solids from Molecular Building Blocks: Golden Opportunities for Solid State Chemistry journal, June 2000

Reticular synthesis and the design of new materials journal, June 2003

Metal–organic Frameworks: A tale of two entanglements journal, February 2007

Reticular Chemistry and Metal-Organic Frameworks for Clean Energy journal, September 2009

Docking in Metal-Organic Frameworks journal, August 2009

Thermal conductivity of a metal-organic framework (MOF-5): Part II. Measurement journal, February 2007

Metal-organic frameworks—New materials for hydrogen storage journal, April 2007

Impact of Preparation and Handling on the Hydrogen Storage Properties of Zn4O(1,4-benzenedicarboxylate)3 (MOF-5) journal, November 2007

Assembly of Metal−Organic Frameworks from Large Organic and Inorganic Secondary Building Units: New Examples and Simplifying Principles for Complex Structures journal, August 2001

A Crystalline Mesoporous Coordination Copolymer with High Microporosity journal, January 2008

Coordinatively Unsaturated Metal Centers in the Extended Porous Framework of Zn3(BDC)3·6CH3OH (BDC = 1,4-Benzenedicarboxylate) journal, March 1998

Establishing Microporosity in Open Metal−Organic Frameworks: Gas Sorption Isotherms for Zn(BDC) (BDC = 1,4-Benzenedicarboxylate) journal, August 1998

Design and synthesis of an exceptionally stable and highly porous metal-organic framework journal, November 1999

20 Å Cd4In16S3514- Supertetrahedral T4 Clusters as Building Units in Decorated Cristobalite Frameworks journal, May 2001

[Cd16In64S134]44-: 31-Å Tetrahedron with a Large Cavity journal, April 2003

A metal–organic framework replete with ordered donor–acceptor catenanes journal, January 2010

A Catenated Strut in a Catenated Metal-Organic Framework journal, August 2010

The pervasive chemistry of metal–organic frameworks journal, January 2009

Synthesis and Structure of Chemically Stable Metal−Organic Polyhedra journal, September 2009

Adsorption Mechanism and Uptake of Methane in Covalent Organic Frameworks: Theory and Experiment journal, October 2010

Metal−Organic Frameworks with Exceptionally High Capacity for Storage of Carbon Dioxide at Room Temperature journal, December 2005

Crystals as Molecules Postsynthesis Covalent Functionalization of Zeolitic Imidazolate Frameworks journal, September 2008

A Combined Experimental−Computational Investigation of Carbon Dioxide Capture in a Series of Isoreticular Zeolitic Imidazolate Frameworks journal, August 2010

Implementation of a strategy for achieving extraordinary levels of surface area and porosity in crystals
patent, January 2010

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

Palladium-Catalyzed Suzuki-Type Self-Coupling of Arylboronic Acids. A Mechanistic Study
journal, January 1996

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

Isoreticular MOFs based on a rhombic dodecahedral MOP as a tertiary building unit
journal, January 2014

Post-Synthetic Modification of Tagged Metal-Organic Frameworks
journal, October 2008

High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to CO₂ Capture
journal, February 2008

Control of Pore Size and Functionality in Isoreticular Zeolitic Imidazolate Frameworks and their Carbon Dioxide Selective Capture Properties
journal, March 2009

Azulene based metal–organic frameworks for strong adsorption of H₂
journal, January 2010

Tailored Porous Materials
journal, October 1999

Metal Insertion in a Microporous Metal−Organic Framework Lined with 2,2′-Bipyridine
journal, October 2010

1,4-Benzenedicarboxylate derivatives as links in the design of paddle-wheel units and metal–organic frameworks
journal, November 2001

Highly efficient separation of carbon dioxide by a metal-organic framework replete with open metal sites
journal, November 2009

Ring-Opening Reactions within Porous Metal−Organic Frameworks
journal, July 2010

Polycatenation, polythreading and polyknotting in coordination network chemistry
journal, November 2003

Dramatic Tuning of Carbon Dioxide Uptake via Metal Substitution in a Coordination Polymer with Cylindrical Pores
journal, August 2008

Raman spectra of hydrogen and deuterium adsorbed on a metal–organic framework
journal, August 2005

Tertiary Building Units: Synthesis, Structure, and Porosity of a Metal−Organic Dendrimer Framework (MODF-1)
October 2001

MOFs as catalysts: Activity, reusability and shape-selectivity of a Pd-containing MOF
journal, September 2007

A route to high surface area, porosity and inclusion of large molecules in crystals
journal, February 2004

Cu₂(ATC)·6H₂O: Design of Open Metal Sites in Porous Metal−Organic Crystals (ATC: 1,3,5,7-Adamantane Tetracarboxylate)
journal, November 2000

Interwoven Metal-Organic Framework on a Periodic Minimal Surface with Extra-Large Pores
journal, February 2001

Transformation of a Metal−Organic Framework from the NbO to PtS Net
journal, January 2005

High H₂ Adsorption in a Microporous Metal-Organic Framework with Open Metal Sites
journal, July 2005

A Microporous Metal–Organic Framework for Gas-Chromatographic Separation of Alkanes
journal, February 2006

A metal–organic framework material that functions as an enantioselective catalyst for olefin epoxidation
journal, January 2006

Heterogeneity within Order in Crystals of a Porous Metal–Organic Framework
journal, August 2011

In Situ Hydrothermal Growth of Metal−Organic Framework 199 Films on Stainless Steel Fibers for Solid-Phase Microextraction of Gaseous Benzene Homologues
journal, December 2009

Three-periodic nets and tilings: regular and quasiregular nets
journal, December 2002

What do we know about three-periodic nets?
journal, August 2005

Three-periodic nets and tilings: edge-transitive binodal structures
journal, August 2006

Multiple Functional Groups of Varying Ratios in Metal-Organic Frameworks
journal, February 2010

Robust dynamics
journal, May 2010

Isoreticular Metalation of Metal−Organic Frameworks
journal, July 2009

Design of New Materials for Methane Storage
journal, March 2004

Highly Porous and Stable Metal−Organic Frameworks: Structure Design and Sorption Properties
journal, February 2000

Porous Metal−Organic Polyhedra: 25 Å Cuboctahedron Constructed from 12 Cu₂(CO₂)₄ Paddle-Wheel Building Blocks
journal, May 2001

Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal−Organic Carboxylate Frameworks
journal, April 2001

Geometric requirements and examples of important structures in the assembly of square building blocks
journal, April 2002

Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage
journal, January 2002

Cu₂[o-Br-C₆H₃(CO₂)₂]₂(H₂O)₂·(DMF)₈(H₂O)₂: A Framework Deliberately Designed To Have the NbO Structure Type
journal, January 2002

Positronium formation in porous materials for antihydrogen production
journal, April 2010

Independent verification of the saturation hydrogen uptake in MOF-177 and establishment of a benchmark for hydrogen adsorption in metal–organic frameworks
journal, January 2007

Control of Vertex Geometry, Structure Dimensionality, Functionality, and Pore Metrics in the Reticular Synthesis of Crystalline Metal−Organic Frameworks and Polyhedra
journal, September 2008

Storage of Hydrogen, Methane, and Carbon Dioxide in Highly Porous Covalent Organic Frameworks for Clean Energy Applications
journal, July 2009

Ultrahigh Porosity in Metal-Organic Frameworks
journal, July 2010

Adsorption of Harmful Organic Vapors by Flexible Hydrophobic Bis-pyrazolate Based MOFs
journal, March 2010

MOF-74 building unit has a direct impact on toxic gas adsorption
journal, January 2011

Construction of Microporous Materials from Molecular Building Blocks
book, January 2002

Construction of Porous Solids from Hydrogen-Bonded Metal Complexes of 1,3,5-Benzenetricarboxylic Acid
journal, January 1996

Selective Guest Binding by Tailored Channels in a 3-D Porous Zinc(II)−Benzenetricarboxylate Network
journal, March 1997

Crystal Growth of Extended Solids by Nonaqueous Gel Diffusion
journal, May 1997

A Molecular Railroad with Large Pores: Synthesis and Structure of Ni(4,4‘-bpy)_2.5(H₂O)₂(ClO₄)₂·1.5(4,4‘-bpy)·2H₂O
journal, September 1997

Synthetic Strategies, Structure Patterns, and Emerging Properties in the Chemistry of Modular Porous Solids^†
journal, August 1998

Design of Solids from Molecular Building Blocks: Golden Opportunities for Solid State Chemistry
journal, June 2000

Reticular synthesis and the design of new materials
journal, June 2003

Metal–organic Frameworks: A tale of two entanglements
journal, February 2007

Reticular Chemistry and Metal-Organic Frameworks for Clean Energy
journal, September 2009

Docking in Metal-Organic Frameworks
journal, August 2009

Thermal conductivity of a metal-organic framework (MOF-5): Part II. Measurement
journal, February 2007

Metal-organic frameworks—New materials for hydrogen storage
journal, April 2007

Impact of Preparation and Handling on the Hydrogen Storage Properties of Zn₄O(1,4-benzenedicarboxylate)₃ (MOF-5)
journal, November 2007

Assembly of Metal−Organic Frameworks from Large Organic and Inorganic Secondary Building Units: New Examples and Simplifying Principles for Complex Structures
journal, August 2001

A Crystalline Mesoporous Coordination Copolymer with High Microporosity
journal, January 2008

Coordinatively Unsaturated Metal Centers in the Extended Porous Framework of Zn₃(BDC)₃·6CH₃OH (BDC = 1,4-Benzenedicarboxylate)
journal, March 1998

Establishing Microporosity in Open Metal−Organic Frameworks: Gas Sorption Isotherms for Zn(BDC) (BDC = 1,4-Benzenedicarboxylate)
journal, August 1998

Design and synthesis of an exceptionally stable and highly porous metal-organic framework
journal, November 1999

20 Å Cd₄In₁₆S₃₅^14- Supertetrahedral T4 Clusters as Building Units in Decorated Cristobalite Frameworks
journal, May 2001

[Cd₁₆In₆₄S₁₃₄]^44-: 31-Å Tetrahedron with a Large Cavity
journal, April 2003

A metal–organic framework replete with ordered donor–acceptor catenanes
journal, January 2010

A Catenated Strut in a Catenated Metal-Organic Framework
journal, August 2010

The pervasive chemistry of metal–organic frameworks
journal, January 2009

Synthesis and Structure of Chemically Stable Metal−Organic Polyhedra
journal, September 2009

Adsorption Mechanism and Uptake of Methane in Covalent Organic Frameworks: Theory and Experiment
journal, October 2010

Metal−Organic Frameworks with Exceptionally High Capacity for Storage of Carbon Dioxide at Room Temperature
journal, December 2005

Crystals as Molecules Postsynthesis Covalent Functionalization of Zeolitic Imidazolate Frameworks
journal, September 2008

A Combined Experimental−Computational Investigation of Carbon Dioxide Capture in a Series of Isoreticular Zeolitic Imidazolate Frameworks
journal, August 2010

Postsynthetic Modification of a Metal–Organic Framework for Stabilization of a Hemiaminal and Ammonia Uptake
journal, August 2011

Non-carboxylate based metal-organic frameworks (MOFs) and related aspects
journal, June 2009

Porous Metal−Organic Truncated Octahedron Constructed from Paddle-Wheel Squares and Terthiophene Links
journal, September 2005