Leveraging of Sulfur Anions in Photoinduced Molecular Transformations

Review Chemistry, Multidisciplinary

Excited State Anions in Organic Transformations

Matthias Schmalzbauer et al.

Summary: Utilizing photoexcited anionic species in organic synthesis has great potential to open up novel and unique pathways in organic chemistry, leading to more sustainable and atom-economic chemical processes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

Haoyu Li et al.

Summary: This study reveals the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. By photoexcitation of tetrasulfide dianions, single-electron reduction of aryl halides is achieved, leading to the participation of aryl radicals in cross-coupling, borylation, and hydrogenation reactions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Physical

Dual-Role Catalysis by Thiobenzoic Acid in Cα-H Arylation under Photoirradiation

Fumihisa Kobayashi et al.

Summary: Thiobenzoic acid (TBA) can act as a single-electron reducing agent under blue light irradiation, enabling regioselective C alpha-H arylation of benzylamines, benzyl alcohols, ethers, and dihydroimidazoles through dual-role catalysis.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Mechanistic Investigations of an α-Aminoarylation Photoredox Reaction

Bernard G. Stevenson et al.

Summary: While photoredox catalysis has been influential in modern synthetic chemistry, a detailed mechanistic study of alpha-aminoarylation mechanism reveals its complexity and low external quantum yield despite high product yields. The use of transient absorption spectroscopy allowed for identification of productive and unproductive reaction pathways and assignment of rate constants, providing a comprehensive understanding of the reaction. Kinetic modeling showed that the reaction is limited by scattering losses and parasitic absorption rather than individual kinetics steps.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes

Eduardo de Pedro Beato et al.

Summary: The study introduces a modular class of organic catalysts that can form photoactive electron donor-acceptor complexes with radical precursors. Excitation with visible light generates open-shell intermediates, allowing for the development of mechanistically distinct radical reactions encompassing redox-neutral and net-reductive processes. The organic catalysts demonstrate the ability to turn over and iteratively drive every catalytic cycle, enabling direct radical functionalization and enantioselective radical catalysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Shun Wang et al.

Summary: Efforts are being made to develop photo-redox catalysts with high redox power, although current methods face challenges in activating bonds with high bond dissociation energy and substrates with high reduction potentials. A novel photocatalytic strategy using thiolate as a catalyst has been introduced for the activation of inert substituted arenes for aryl borylation, expanding the scope of aryl radical precursors and demonstrating good functional-group tolerance. Spectroscopic investigations suggest the formation of a charge-transfer complex as the key step to activate the substrates.

CHEM (2021)

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Article Chemistry, Multidisciplinary

Visible-Light-Driven C-S Bond Formation Based on Electron Donor- Acceptor Excitation and Hydrogen Atom Transfer Combined System

Tatsuhiro Uchikura et al.

Summary: This study introduces a visible-light-driven synthesis of sulfides without the use of transition metals and strong oxidants. The reaction involves the excitation of an electron donor-acceptor complex between a thiolate and an aryl halide, followed by hydrogen atom transfer from an alkane to the generated aryl radical.

ACS ORGANIC & INORGANIC AU (2021)

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Article Chemistry, Multidisciplinary

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

Haoyu Li et al.

Summary: A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been successfully developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

CHEMICAL COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

Aromatic Chemistry in the Excited State: Facilitating Metal-Free Substitutions and Cross-Couplings

Wenbo Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals

Davide Spinnato et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Review Chemistry, Multidisciplinary

Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes

Giacomo E. M. Crisenza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Multidisciplinary Sciences

Chemistry glows green with photoredox catalysis

Giacomo E. M. Crisenza et al.

NATURE COMMUNICATIONS (2020)

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Article Polymer Science

Discovery of the RAFT/MADIX Process: Mechanistic Insights and Polymer Chemistry Implications

Samir Z. Zard

MACROMOLECULES (2020)

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Review Chemistry, Multidisciplinary

Photoinduced deaminative strategies: Katritzky salts as alkyl radical precursors

Jose Tiago M. Correia et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof

Eduardo de Pedro Beato et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Physical

Photochemical Organocatalytic Borylation of Alkyl Chlorides, Bromides, and Sulfonates

Daniele Mazzarella et al.

ACS CATALYSIS (2019)

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Review Chemistry, Multidisciplinary

Radical Alliances: Solutions and Opportunities for Organic Synthesis

Samir Z. Zard

HELVETICA CHIMICA ACTA (2019)

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Article Chemistry, Organic

Photocatalyst-Free Visible-Light-Promoted C(sp2)-S Coupling: A Strategy for the Preparation of S-Aryl Dithiocarbamates

Guoqing Li et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Visible-Light-Induced Deaminative Thioesterification of Amino Acid Derived Katritzky Salts via Electron Donor-Acceptor Complex Formation

Mingcheng Yang et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

Photochemical generation of radicals from alkyl electrophiles using a nucleophilic organic catalyst

Bertrand Schweitzer-Chaput et al.

NATURE CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

Sara Cuadros et al.

CHEMICAL SCIENCE (2019)

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Review Chemistry, Multidisciplinary

Illuminating Photoredox Catalysis

Rory C. McAtee et al.

TRENDS IN CHEMISTRY (2019)

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Article Chemistry, Physical

Site-Selective C-H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope

Davide Ravelli et al.

ACS CATALYSIS (2018)

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Review Chemistry, Multidisciplinary

Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?

Leyre Marzo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Review Chemistry, Organic

Photocatalytic formation of carbon-sulfur bonds

Alexander Wimmer et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Reflections on the mechanism of the Barton-McCombie Deoxygenation and on its consequences

Stuart W. McCombie et al.

TETRAHEDRON (2018)

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Article Chemistry, Multidisciplinary

Metal-Free Radical Borylation of Alkyl and Aryl Iodides

Ying Cheng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer

Bin Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

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Article Chemistry, Organic

Experimental and Calculated Electrochemical Potentials of Common Organic Molecules for Applications to Single-Electron Redox Chemistry

Hudson G. Roth et al.

SYNLETT (2016)

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Review Chemistry, Multidisciplinary

Carbon-Carbon Bond Forming Reactions via Photogenerated Intermediates

Davide Ravelli et al.

CHEMICAL REVIEWS (2016)

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Review Chemistry, Multidisciplinary

Organic Photoredox Catalysis

Nathan A. Romero et al.

CHEMICAL REVIEWS (2016)

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Article Chemistry, Organic

Photoredox Catalysis in Organic Chemistry

Megan H. Shaw et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Physical

Solvent-Dictated Lithium Sulfur Redox Reactions: An Operando UV-vis Spectroscopic Study

Qingli Zou et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2016)

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Review Chemistry, Organic

The xanthate route to organofluorine derivatives. A brief account

Samir Z. Zard

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

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Review Chemistry, Multidisciplinary

Thiyl Radicals in Organic Synthesis

Fabrice Denes et al.

CHEMICAL REVIEWS (2014)

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Article Chemistry, Multidisciplinary

Mechanistic Insight into the Photoredox Catalysis of Anti-Markovnikov Alkene Hydrofunctionalization Reactions

Nathan A. Romero et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Review Multidisciplinary Sciences

Solar Synthesis: Prospects in Visible Light Photocatalysis

Danielle M. Schultz et al.

SCIENCE (2014)

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Article Polymer Science

Use of spin traps to measure the addition and fragmentation rate coefficients of small molecule RAFT-adduct radicals

Elena Chernikova et al.

POLYMER CHEMISTRY (2010)

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Article Chemistry, Organic

Mechanism of SH2 Reactions of Disulfides: Frontside vs Backside, Stepwise vs Concerted

Elizabeth H. Krenske et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

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Review Chemistry, Multidisciplinary

The genesis of the reversible radical addition-fragmentation-transfer of thiocarbonylthio derivatives from the Barton-McCombie deoxygenation: A brief account and some mechanistic observations

Samir Z. Zard

AUSTRALIAN JOURNAL OF CHEMISTRY (2006)

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Review Chemistry, Multidisciplinary

Faster dissociation: Measured rates and computed effects on barriers in aryl halide radical anions

N Takeda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Multidisciplinary

Fragmentation of aryl halide π anion radicals.: Bending of the cleaving bond and activation vs driving force relationships

C Costentin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Review Chemistry, Multidisciplinary

Nucleophilic substitution reactions by electron transfer

RA Rossi et al.

CHEMICAL REVIEWS (2003)

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Article Electrochemistry

Comments on the mechanism of the electrochemical reduction of sulphur in dimethylformamide

P Leghié et al.

ELECTROCHEMISTRY COMMUNICATIONS (2002)

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Leveraging of Sulfur Anions in Photoinduced Molecular Transformations

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