Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes

Vasilopoulos, Aristidis; Zultanski, Susan L.; Stahl, Shannon S.

doi:10.1021/jacs.7b03387

Title: Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes

Abstract

A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C–H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C–H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. In conclusion, the potential utility of these methods in medicinal chemistry applications is highlighted.

Authors:

Vasilopoulos, Aristidis ^[1]; Zultanski, Susan L. ^[2];

^[1]

Univ. of Wisconsin-Madison, Madison, WI (United States)
Univ. of Wisconsin-Madison, Madison, WI (United States); Merck & Co., Inc., Rahway, NJ (United States)

Publication Date:: Tue May 30 00:00:00 EDT 2017

Research Org.:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1471697

Grant/Contract Number:: FG02-05ER15690

Resource Type:: Accepted Manuscript

Journal Name:: Journal of the American Chemical Society

Additional Journal Information:: Journal Volume: 139; Journal Issue: 23; Journal ID: ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Vasilopoulos, Aristidis, Zultanski, Susan L., and Stahl, Shannon S. Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes.  United States: N. p., 2017. 
Web.  doi:10.1021/jacs.7b03387.

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                    Vasilopoulos, Aristidis, Zultanski, Susan L., & Stahl, Shannon S. Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes.  United States.  https://doi.org/10.1021/jacs.7b03387

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                    Vasilopoulos, Aristidis, Zultanski, Susan L., and Stahl, Shannon S. Tue .  
"Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes".  United States.  https://doi.org/10.1021/jacs.7b03387.  https://www.osti.gov/servlets/purl/1471697.

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@article{osti_1471697,

  title        = {Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes},

  author       = {Vasilopoulos, Aristidis and Zultanski, Susan L. and Stahl, Shannon S.},

  abstractNote = {A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C–H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C–H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. In conclusion, the potential utility of these methods in medicinal chemistry applications is highlighted.},

  doi          = {10.1021/jacs.7b03387},

  journal      = {Journal of the American Chemical Society},

  number       = 23,

  volume       = 139,

  place        = {United States},

  year         = {Tue May 30 00:00:00 EDT 2017},

  month        = {Tue May 30 00:00:00 EDT 2017}

}

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Wang, Zhiting; Zheng, Zhipeng; Xu, Xinyu
Nature Communications, Vol. 9, Issue 1
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Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters
journal, March 2018

Moon, Patrick J.; Fahandej‐Sadi, Anis; Qian, Wenyu
Angewandte Chemie, Vol. 130, Issue 17
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Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine‐Directed para and ortho C−H Functionalization
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Wu, Yichen; Bouvet, Sébastien; Izquierdo, Susana
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One-pot aminobenzylation of aldehydes with toluenes
journal, August 2018

Wang, Zhiting; Zheng, Zhipeng; Xu, Xinyu
Nature Communications, Vol. 9, Issue 1
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A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes
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Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
journal, January 2018

Chen, Qiao; Zhu, Tingshun; Majhi, Pankaj Kumar
Chemical Science, Vol. 9, Issue 46
DOI: 10.1039/c8sc03480j

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Title: Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes

Abstract

Citation Formats

Utilization of methylarenes as versatile building blocks in organic synthesis journal, January 2015

Copper-Catalyzed Oxidative Coupling of Benzylic C−H Bonds with 1,3-Dicarbonyl Compounds journal, September 2008

Four Tandem C–H Activations: A Sequential C–C and C–O Bond Making via a Pd-Catalyzed Cross Dehydrogenative Coupling (CDC) Approach journal, September 2012

Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides journal, January 2013

Palladium-Catalyzed Cascade Oxidation/ sp 2 C–H Acylation of Azoarenes with Aryl Methanes journal, October 2013

Palladium catalyzed direct ortho C–H acylation of 2-arylpyridines using toluene derivatives as acylation reagents journal, January 2013

Chemoselective Activation of sp 3 vs sp 2 C–H Bonds with Pd(II) journal, December 2014

Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes journal, June 2016

Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations journal, February 2009

Nickel-Catalyzed Selective Oxidative Radical Cross-Coupling: An Effective Strategy for Inert Csp 3 –H Functionalization journal, February 2015

Substituted 1,1-diphenyl-3-aminoprop-1-enes and 1,1-diphenyl-3-aminopropanes as potential antidepressant agents journal, February 1971

Histamine and the antiallergic antihistamines: a history of their discoveries: History of antiallergic antihistamines journal, July 1999

Pharmacology of Antihistamines journal, January 2011

Discovery of Isoerianin Analogues as Promising Anticancer Agents journal, January 2011

Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity journal, June 2012

Ni(II)-Catalyzed Oxidative Coupling between C(sp 2 )–H in Benzamides and C(sp 3 )–H in Toluene Derivatives journal, October 2014

Pd(II)-catalyzed Chelation-assisted Cross Dehydrogenative Coupling between Unactivated C(sp 3 )–H Bonds in Aliphatic Amides and Benzylic C–H Bonds in Toluene Derivatives journal, October 2015

Copper-Catalyzed Direct C2-Benzylation of Indoles with Alkylarenes journal, November 2015

Photoinduced direct 4-pyridination of C(sp3)–H Bonds journal, January 2013

Direct C(sp 3 )–H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals journal, September 2016

Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations journal, September 2016

Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles journal, April 2016

THE REACTIONS OF t-BUTYL PERBENZOATE AND OLEFINS—A STEREOSPECIFIC REACTION 1 journal, February 1958

Communications - Radical Substitution Reactions journal, February 1958

One-Step Substitutive Acyloxylation at Carbon. Part I. Reactions Involving Peroxides journal, January 1972

Catalytic Allylic Oxidation of Alkenes Using an Asymmetric Kharasch–Sosnovsky Reaction journal, October 2001

Copper catalyzed allylic oxidation with peresters journal, January 2002

Studies on the Mechanism of the Reaction of Peroxides and Alkenes with Copper Salts *,1 journal, June 1965

Homolytic and ionic mechanisms in the ligand-transfer oxidation of alkyl radicals by copper(II) halides and pseudohalides journal, February 1972

Reaction of Cu I with Dialkyl Peroxides: Cu II -Alkoxides, Alkoxy Radicals, and Catalytic C–H Etherification journal, October 2012

Copper-Catalyzed Oxidative Dehydrogenative Carboxylation of Unactivated Alkanes to Allylic Esters via Alkenes journal, November 2014

Copper-Catalyzed Intermolecular Amidation and Imidation of Unactivated Alkanes journal, January 2014

Copper-Catalyzed Amination of Primary Benzylic C−H Bonds with Primary and Secondary Sulfonamides journal, March 2010

Allylic Oxidation of Alkenes Catalyzed by a Copper–Aluminum Mixed Oxide journal, March 2014

Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes journal, August 2015

Esterification of the Primary Benzylic C–H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation journal, February 2017

Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay journal, September 2016

Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II) journal, August 2012

Copper-Catalyzed Intermolecular Trifluoromethylarylation of Alkenes: Mutual Activation of Arylboronic Acid and CF 3 + Reagent journal, July 2014

Benzofuran Derivatives as Potent, Orally Active S1P 1 Receptor Agonists: A Preclinical Lead Molecule for MS journal, November 2010

An improved asymmetric synthetic route to a novel triple uptake inhibitor antidepressant (2S,4R,5R)-2-benzhydryl-5-((4-methoxybenzyl)amino)tetrahydro-2H-pyran-4-ol (D-142) journal, May 2011

Palladium-Catalyzed C(sp 3 )–H Arylation of Diarylmethanes at Room Temperature: Synthesis of Triarylmethanes via Deprotonative-Cross-Coupling Processes journal, August 2012

NiXantphos: A Deprotonatable Ligand for Room-Temperature Palladium-Catalyzed Cross-Couplings of Aryl Chlorides journal, April 2014

Free-Radical Bromination of Selected Organic Compounds in Water journal, January 1997

DDQ-Catalyzed Oxidative CO Coupling Of sp 3 CH Bonds With Carboxylic Acids journal, November 2012

A Scalable Procedure for Light-Induced Benzylic Brominations in Continuous Flow journal, November 2013

I − /TBHP catalyzed C sp3 –N/C sp2 –N bond formation via oxidative coupling with benzophenone imine in water journal, January 2015

Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules journal, January 2017

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes journal, October 2013

Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation journal, December 2012

Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes journal, February 2013

A general, simple catalyst for enantiospecific cross couplings of benzylic ammonium triflates and boronic acids: no phosphine ligand required journal, July 2014

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis journal, June 2014

Der “Persistent Radical Effect” in der organischen Chemie journal, January 2020

Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine-Directed para and ortho C−H Functionalization journal, December 2018

Enantioselective Arylation of Benzylic C−H Bonds by Copper‐Catalyzed Radical Relay journal, February 2019

Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations journal, July 2018

Copper‐Catalyzed Arylation of Remote C(sp 3 )−H Bonds in Carboxamides and Sulfonamides journal, September 2018

Enantioselective Arylation of Benzylic C−H Bonds by Copper-Catalyzed Radical Relay journal, April 2019

Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis journal, August 2019

Unsymmetrical CNN-palladacycles with geometry-constrained iminopyridyl ligands: an efficient precatalyst in Suzuki coupling for accessing 1,1-diarylalkanes from secondary benzylic bromides journal, January 2018

Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp 3 C–H functionalization of azaarenes journal, January 2019

Copper‐Catalyzed Radical Cross‐Coupling of Redox‐Active Oxime Esters, Styrenes, and Boronic Acids journal, November 2018

Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones journal, October 2018

A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds journal, January 2019

Expanding the limit of Pd-catalyzed decarboxylative benzylations journal, January 2018

Oxidative C(sp 3 )–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3- a ]pyridines journal, January 2019

Remote C(sp 3 )−H Arylation and Vinylation of N ‐Alkoxypyridinium Salts to δ‐Aryl and δ‐Vinyl Alcohols journal, August 2019

The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C−H Arylations: Hydrogen-Atom Transfer and Energy Transfer journal, February 2019

The Persistent Radical Effect in Organic Synthesis journal, January 2020

A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes journal, August 2018

1,10‐Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal‐Organic Frameworks journal, September 2019

Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters journal, March 2018

Copper‐Catalyzed Radical Cross‐Coupling of Redox‐Active Oxime Esters, Styrenes, and Boronic Acids journal, November 2018

Hybrid Reaction Systems for the Synthesis of Alkylated Compounds Based upon Cu‐Catalyzed Coupling of Radicals and Organometallic Species journal, September 2019

Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes journal, January 2018

Copper‐Catalyzed Arylation of Remote C(sp 3 )−H Bonds in Carboxamides and Sulfonamides journal, October 2018

Utilization of methylarenes as versatile building blocks in organic synthesis
journal, January 2015

Copper-Catalyzed Oxidative Coupling of Benzylic C−H Bonds with 1,3-Dicarbonyl Compounds
journal, September 2008

Four Tandem C–H Activations: A Sequential C–C and C–O Bond Making via a Pd-Catalyzed Cross Dehydrogenative Coupling (CDC) Approach
journal, September 2012

Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides
journal, January 2013

Palladium-Catalyzed Cascade Oxidation/ sp ² C–H Acylation of Azoarenes with Aryl Methanes
journal, October 2013

Palladium catalyzed direct ortho C–H acylation of 2-arylpyridines using toluene derivatives as acylation reagents
journal, January 2013

Chemoselective Activation of sp ³ vs sp ² C–H Bonds with Pd(II)
journal, December 2014

Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes
journal, June 2016

Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations
journal, February 2009

Nickel-Catalyzed Selective Oxidative Radical Cross-Coupling: An Effective Strategy for Inert Csp ³ –H Functionalization
journal, February 2015

Substituted 1,1-diphenyl-3-aminoprop-1-enes and 1,1-diphenyl-3-aminopropanes as potential antidepressant agents
journal, February 1971

Histamine and the antiallergic antihistamines: a history of their discoveries: History of antiallergic antihistamines
journal, July 1999

Pharmacology of Antihistamines
journal, January 2011

Discovery of Isoerianin Analogues as Promising Anticancer Agents
journal, January 2011

Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity
journal, June 2012

Ni(II)-Catalyzed Oxidative Coupling between C(sp ² )–H in Benzamides and C(sp ³ )–H in Toluene Derivatives
journal, October 2014

Pd(II)-catalyzed Chelation-assisted Cross Dehydrogenative Coupling between Unactivated C(sp ³ )–H Bonds in Aliphatic Amides and Benzylic C–H Bonds in Toluene Derivatives
journal, October 2015

Copper-Catalyzed Direct C2-Benzylation of Indoles with Alkylarenes
journal, November 2015

Photoinduced direct 4-pyridination of C(sp3)–H Bonds
journal, January 2013

Direct C(sp ³ )–H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals
journal, September 2016

Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations
journal, September 2016

Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles
journal, April 2016

THE REACTIONS OF t-BUTYL PERBENZOATE AND OLEFINS—A STEREOSPECIFIC REACTION ¹
journal, February 1958

Communications - Radical Substitution Reactions
journal, February 1958

One-Step Substitutive Acyloxylation at Carbon. Part I. Reactions Involving Peroxides
journal, January 1972

Catalytic Allylic Oxidation of Alkenes Using an Asymmetric Kharasch–Sosnovsky Reaction
journal, October 2001

Copper catalyzed allylic oxidation with peresters
journal, January 2002

Studies on the Mechanism of the Reaction of Peroxides and Alkenes with Copper Salts ^*,1
journal, June 1965

Homolytic and ionic mechanisms in the ligand-transfer oxidation of alkyl radicals by copper(II) halides and pseudohalides
journal, February 1972

Reaction of Cu ^I with Dialkyl Peroxides: Cu ^II -Alkoxides, Alkoxy Radicals, and Catalytic C–H Etherification
journal, October 2012

Copper-Catalyzed Oxidative Dehydrogenative Carboxylation of Unactivated Alkanes to Allylic Esters via Alkenes
journal, November 2014

Copper-Catalyzed Intermolecular Amidation and Imidation of Unactivated Alkanes
journal, January 2014

Copper-Catalyzed Amination of Primary Benzylic C−H Bonds with Primary and Secondary Sulfonamides
journal, March 2010

Allylic Oxidation of Alkenes Catalyzed by a Copper–Aluminum Mixed Oxide
journal, March 2014

Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes
journal, August 2015

Esterification of the Primary Benzylic C–H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation
journal, February 2017

Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay
journal, September 2016

Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II)
journal, August 2012

Copper-Catalyzed Intermolecular Trifluoromethylarylation of Alkenes: Mutual Activation of Arylboronic Acid and CF ₃ ⁺ Reagent
journal, July 2014

Benzofuran Derivatives as Potent, Orally Active S1P ₁ Receptor Agonists: A Preclinical Lead Molecule for MS
journal, November 2010

An improved asymmetric synthetic route to a novel triple uptake inhibitor antidepressant (2S,4R,5R)-2-benzhydryl-5-((4-methoxybenzyl)amino)tetrahydro-2H-pyran-4-ol (D-142)
journal, May 2011

Palladium-Catalyzed C(sp ³ )–H Arylation of Diarylmethanes at Room Temperature: Synthesis of Triarylmethanes via Deprotonative-Cross-Coupling Processes
journal, August 2012

NiXantphos: A Deprotonatable Ligand for Room-Temperature Palladium-Catalyzed Cross-Couplings of Aryl Chlorides
journal, April 2014

Free-Radical Bromination of Selected Organic Compounds in Water
journal, January 1997

DDQ-Catalyzed Oxidative CO Coupling Of sp ³ CH Bonds With Carboxylic Acids
journal, November 2012

A Scalable Procedure for Light-Induced Benzylic Brominations in Continuous Flow
journal, November 2013

I ⁻ /TBHP catalyzed C _sp3 –N/C _sp2 –N bond formation via oxidative coupling with benzophenone imine in water
journal, January 2015

Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules
journal, January 2017

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
journal, October 2013

Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation
journal, December 2012

Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes
journal, February 2013

A general, simple catalyst for enantiospecific cross couplings of benzylic ammonium triflates and boronic acids: no phosphine ligand required
journal, July 2014

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
journal, June 2014

Der “Persistent Radical Effect” in der organischen Chemie
journal, January 2020

Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine-Directed para and ortho C−H Functionalization
journal, December 2018

Enantioselective Arylation of Benzylic C−H Bonds by Copper‐Catalyzed Radical Relay
journal, February 2019

Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations
journal, July 2018

Copper‐Catalyzed Arylation of Remote C(sp ³ )−H Bonds in Carboxamides and Sulfonamides
journal, September 2018

Enantioselective Arylation of Benzylic C−H Bonds by Copper-Catalyzed Radical Relay
journal, April 2019

Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
journal, August 2019

Unsymmetrical CNN-palladacycles with geometry-constrained iminopyridyl ligands: an efficient precatalyst in Suzuki coupling for accessing 1,1-diarylalkanes from secondary benzylic bromides
journal, January 2018

Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp ³ C–H functionalization of azaarenes
journal, January 2019

Copper‐Catalyzed Radical Cross‐Coupling of Redox‐Active Oxime Esters, Styrenes, and Boronic Acids
journal, November 2018

Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones
journal, October 2018

A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds
journal, January 2019

Expanding the limit of Pd-catalyzed decarboxylative benzylations
journal, January 2018

Oxidative C(sp ³ )–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3- a ]pyridines
journal, January 2019

Remote C(sp ³ )−H Arylation and Vinylation of N ‐Alkoxypyridinium Salts to δ‐Aryl and δ‐Vinyl Alcohols
journal, August 2019

The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C−H Arylations: Hydrogen-Atom Transfer and Energy Transfer
journal, February 2019

The Persistent Radical Effect in Organic Synthesis
journal, January 2020

A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes
journal, August 2018

1,10‐Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal‐Organic Frameworks
journal, September 2019

Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters
journal, March 2018

Copper‐Catalyzed Radical Cross‐Coupling of Redox‐Active Oxime Esters, Styrenes, and Boronic Acids
journal, November 2018

Hybrid Reaction Systems for the Synthesis of Alkylated Compounds Based upon Cu‐Catalyzed Coupling of Radicals and Organometallic Species
journal, September 2019

Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
journal, January 2018

Copper‐Catalyzed Arylation of Remote C(sp ³ )−H Bonds in Carboxamides and Sulfonamides
journal, October 2018

Organocatalytic decarboxylative alkylation of N -hydroxy-phthalimide esters enabled by pyridine-boryl radicals
journal, January 2018

Cu‐Catalyzed Cross‐Dehydrogenative ortho ‐Aminomethylation of Phenols
journal, September 2018

Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
journal, January 2018