Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

doi:https://doi.org/10.1039/C8QO00938D

Title: Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

Abstract

A metal-free synthesis of biaryl compounds was achieved under photo-irradiation, which represents a milder alternative for cross-coupling reactions.

Authors:

Barragan, Enrique ^[1]; Noonikara Poyil, Anurag ^[1];

^[2];

^[1]

Department of Chemistry and Biochemistry; University of Texas at Arlington; Arlington; USA
Department of Chemistry; University of Colorado Denver; Denver; USA

Publication Date:: 2019-01-01

Research Org.:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1544131

Resource Type:: Journal Article

Journal Name:: Organic Chemistry Frontiers (Online)

Additional Journal Information:: Journal Volume: 6; Journal Issue: 2; Journal ID: ISSN 2052-4129

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Citation Formats


                    Barragan, Enrique, Noonikara Poyil, Anurag, Yang, Chou-Hsun, Wang, Haobin, and Bugarin, Alejandro. Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation.  United States: N. p., 2019. 
        Web.  doi:10.1039/C8QO00938D.

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                    Barragan, Enrique, Noonikara Poyil, Anurag, Yang, Chou-Hsun, Wang, Haobin, & Bugarin, Alejandro. Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation.  United States.  https://doi.org/10.1039/C8QO00938D

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                    Barragan, Enrique, Noonikara Poyil, Anurag, Yang, Chou-Hsun, Wang, Haobin, and Bugarin, Alejandro. Tue .  
        "Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation".  United States.  https://doi.org/10.1039/C8QO00938D.

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@article{osti_1544131,

  title        = {Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation},

  author       = {Barragan, Enrique and Noonikara Poyil, Anurag and Yang, Chou-Hsun and Wang, Haobin and Bugarin, Alejandro},

  abstractNote = {A metal-free synthesis of biaryl compounds was achieved under photo-irradiation, which represents a milder alternative for cross-coupling reactions.},

  doi          = {10.1039/C8QO00938D},

  url          = {https://www.osti.gov/biblio/1544131},
  journal      = {Organic Chemistry Frontiers (Online)},

  issn         = {2052-4129},

  number       = 2,

  volume       = 6,

  place        = {United States},

  year         = {2019},

  month        = {1}

}

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https://doi.org/10.1039/C8QO00938D

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Works referenced in this record:

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Title: Metal-free cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

Abstract

Citation Formats

1908: Giacomo Ciamician and the Concept of Green Chemistry journal, February 2008

Green chemistry and photochemistry were born at the same time journal, January 2004

The Beginnings of Organic Photochemistry journal, September 1989

The Photochemistry of the Future journal, September 1912

Organic Photoredox Catalysis journal, June 2016

Photoisomerization dynamics of stilbenes journal, May 1991

Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions and Their Application in Synthesis journal, May 1998

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Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy journal, November 2012

Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides journal, March 2018

A Visible-Light-Driven Iminyl Radical-Mediated C−C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters journal, December 2017

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

Tetra- ortho -Substituted Biaryls through Palladium-Catalyzed Suzuki−Miyaura Couplings with a Diaminochlorophosphine Ligand journal, March 2010

Copper-Catalyzed Suzuki–Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates journal, February 2014

Facile Synthesis of Highly Stable Gold Nanoparticles and Their Unexpected Excellent Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reaction in Water journal, February 2009

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl halides journal, January 2004

Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides journal, May 1977

Magical Power of Transition Metals: Past, Present, and Future (Nobel Lecture) journal, June 2011

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Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion journal, February 2004

Aqueous Sodium Hydroxide Promoted Cross-Coupling Reactions of Alkenyltrialkoxysilanes under Ligand-Free Conditions † journal, March 2008

MIDA–Vinylsilanes: Selective Cross-Couplings and Applications to the Synthesis of Functionalized Stilbenes journal, December 2014

The Eight Criteria Defining a Good Chemical Manufacturing Process journal, October 2012

Phenyl Hydrazine as Initiator for Direct Arene C–H Arylation via Base Promoted Homolytic Aromatic Substitution journal, November 2013

Palladium-Catalyzed Arylation of Simple Arenes with Iodonium Salts journal, March 2013

Radical Arylation of Anilines and Pyrroles via Aryldiazotates journal, June 2017

Detection of Aryl Radicals in Hydrodediazoniations † journal, November 1997

Dediazoniation of 4-Nitrobenzenediazonium Ions in Acidic MeOH/H2O Mixtures: Role of Acidity and MeOH Concentration on the Formation of Transient Diazo Ethers that Initiate Homolytic Dediazoniation journal, May 2006

Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical journal, August 1988

Novel triazene dyes from N-heterocyclic carbenes and azides: syntheses, stability, and spectroscopic properties journal, August 2014

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions journal, January 2017

Crystal structure of ( E )-1,3-dimethyl-2-[3-(3-nitrophenyl)triaz-2-en-1-ylidene]-2,3-dihydro-1 H -imidazole journal, September 2014

Fifty Years of π-Conjugated Triaz­enes: Fifty Years of π-Conjugated Triazenes journal, December 2015

Water-Soluble Triazabutadienes that Release Diazonium Species upon Protonation under Physiologically Relevant Conditions journal, February 2015

A Photobasic Functional Group journal, July 2015

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Potassium tert -Butoxide Promoted Intramolecular Arylation via a Radical Pathway journal, June 2011

Donor−Acceptor Triazenes: Synthesis, Characterization, and Study of Their Electronic and Thermal Properties journal, December 2007

Advances in molecular quantum chemistry contained in the Q-Chem 4 program package journal, September 2014

Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model journal, March 1998

Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model journal, April 2003

Robust and variational fitting journal, January 2000

Auxiliary basis expansions for large-scale electronic structure calculations journal, April 2005

Calculation of electronic coupling matrix elements for ground and excited state electron transfer reactions: Comparison of the generalized Mulliken–Hush and block diagonalization methods journal, June 1997

Generalization of the Mulliken-Hush treatment for the calculation of electron transfer matrix elements journal, January 1996

The Sandmeyer Reaction. journal, April 1947

Phase-transfer-catalyzed Gomberg-Bachmann synthesis of unsymmetrical biarenes: a survey of catalysts and substrates journal, May 1984

1908: Giacomo Ciamician and the Concept of Green Chemistry
journal, February 2008

Green chemistry and photochemistry were born at the same time
journal, January 2004

The Beginnings of Organic Photochemistry
journal, September 1989

The Photochemistry of the Future
journal, September 1912

Organic Photoredox Catalysis
journal, June 2016

Photoisomerization dynamics of stilbenes
journal, May 1991

Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions and Their Application in Synthesis
journal, May 1998

Synthetic applications of intramolecular enone-olefin photocycloadditions
journal, December 1988

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy
journal, November 2012

Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides
journal, March 2018

A Visible-Light-Driven Iminyl Radical-Mediated C−C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters
journal, December 2017

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journal, May 2002

Tetra- ortho -Substituted Biaryls through Palladium-Catalyzed Suzuki−Miyaura Couplings with a Diaminochlorophosphine Ligand
journal, March 2010

Copper-Catalyzed Suzuki–Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates
journal, February 2014

Facile Synthesis of Highly Stable Gold Nanoparticles and Their Unexpected Excellent Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reaction in Water
journal, February 2009

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl halides
journal, January 2004

Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides
journal, May 1977

Magical Power of Transition Metals: Past, Present, and Future (Nobel Lecture)
journal, June 2011

Cross-Coupling of Aryltrimethylammonium Iodides with Arylzinc Reagents Catalyzed by Amido Pincer Nickel Complexes
journal, March 2012

Efficient Stille Cross-Coupling Reaction Catalyzed by the Pd(OAc) ₂ /Dabco Catalytic System
journal, April 2005

Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion
journal, February 2004

Aqueous Sodium Hydroxide Promoted Cross-Coupling Reactions of Alkenyltrialkoxysilanes under Ligand-Free Conditions ^†
journal, March 2008

MIDA–Vinylsilanes: Selective Cross-Couplings and Applications to the Synthesis of Functionalized Stilbenes
journal, December 2014

The Eight Criteria Defining a Good Chemical Manufacturing Process
journal, October 2012

Phenyl Hydrazine as Initiator for Direct Arene C–H Arylation via Base Promoted Homolytic Aromatic Substitution
journal, November 2013

Palladium-Catalyzed Arylation of Simple Arenes with Iodonium Salts
journal, March 2013

Radical Arylation of Anilines and Pyrroles via Aryldiazotates
journal, June 2017

Detection of Aryl Radicals in Hydrodediazoniations ^†
journal, November 1997

Dediazoniation of 4-Nitrobenzenediazonium Ions in Acidic MeOH/H2O Mixtures: Role of Acidity and MeOH Concentration on the Formation of Transient Diazo Ethers that Initiate Homolytic Dediazoniation
journal, May 2006

Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical
journal, August 1988

Novel triazene dyes from N-heterocyclic carbenes and azides: syntheses, stability, and spectroscopic properties
journal, August 2014

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions
journal, January 2017

Crystal structure of ( E )-1,3-dimethyl-2-[3-(3-nitrophenyl)triaz-2-en-1-ylidene]-2,3-dihydro-1 H -imidazole
journal, September 2014

Fifty Years of π-Conjugated Triazenes: Fifty Years of π-Conjugated Triazenes
journal, December 2015

Water-Soluble Triazabutadienes that Release Diazonium Species upon Protonation under Physiologically Relevant Conditions
journal, February 2015

A Photobasic Functional Group
journal, July 2015

Hexyl triazabutadiene as a potent alkylating agent
journal, July 2017

Potassium tert -Butoxide Promoted Intramolecular Arylation via a Radical Pathway
journal, June 2011

Donor−Acceptor Triazenes: Synthesis, Characterization, and Study of Their Electronic and Thermal Properties
journal, December 2007

Advances in molecular quantum chemistry contained in the Q-Chem 4 program package
journal, September 2014

Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model
journal, March 1998

Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model
journal, April 2003

Robust and variational fitting
journal, January 2000

Auxiliary basis expansions for large-scale electronic structure calculations
journal, April 2005

Calculation of electronic coupling matrix elements for ground and excited state electron transfer reactions: Comparison of the generalized Mulliken–Hush and block diagonalization methods
journal, June 1997

Generalization of the Mulliken-Hush treatment for the calculation of electron transfer matrix elements
journal, January 1996

The Sandmeyer Reaction.
journal, April 1947

Phase-transfer-catalyzed Gomberg-Bachmann synthesis of unsymmetrical biarenes: a survey of catalysts and substrates
journal, May 1984