4.8 Review

Mechanisms and Synthetic Strategies in Visible Light-Driven [2+2]-Heterocycloadditions

Related references

Note: Only part of the references are listed.
Article Biochemistry & Molecular Biology

Catalyst-free [2+2] photocycloadditions between benzils and olefins under visible light

Roberto Tinelli et al.

Summary: The catalyst-free [2 + 2] photocycloaddition between benzils and simple olefins was investigated to afford the expected oxetanes regio- and stereoselectively; the use of visible light was crucial for enhancing the selectivity of the reaction; lowering the reaction temperature consistently improved the selectivity of the transformation.

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES (2022)

Article Chemistry, Organic

Unlocking the Synthetic Potential of Light-Excited Aryl Ketones: Applications in Direct Photochemistry and Photoredox Catalysis

Javier Mateos et al.

Summary: The group's contributions to photochemistry and photocatalysis have been summarized in this Account, focusing on the development of novel synthetic methods using photoexcited aryl ketones and the application of technologies like microfluidic photoreactors. The careful mechanistic analysis of the developed methods has led to the discovery of a new family of powerful organic photocatalysts that can mediate thermodynamically extreme photoredox processes.

SYNLETT (2022)

Review Chemistry, Multidisciplinary

Enantioselective Photochemical Reactions Enabled by Triplet Energy Transfer

Johannes Grosskopf et al.

Summary: This review provides a comprehensive survey on enantioselective photochemical reactions achieved through triplet sensitization. It is shown that highly selective enantioselective photochemical reactions can be achieved by using appropriate chiral sensitizers or a dual catalytic approach.

CHEMICAL REVIEWS (2022)

Review Chemistry, Multidisciplinary

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Laura Buglioni et al.

Summary: This paper provides a comprehensive overview of the exciting technological advances in the field of photoinduced chemical transformations, including flow chemistry, high-throughput experimentation, reactor design and scale-up, and the combination of photo- and electro-chemistry.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

Intramolecular, Visible-Light-Mediated Aza Paterno-Buchi Reactions of Unactivated Alkenes

Dominique E. Blackmun et al.

Summary: Azetidines are of interest in medicinal chemistry due to their favorable properties, such as increased resistance to oxidative metabolism and lower lipophilicity. The recent development of [2 + 2] reactions has expanded the methods for azetidine synthesis, but further development is needed to access more complex structures.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Preparation of Thietane Derivatives through Domino Photochemical Norrish Type II/Thia-Paterno-Buchi Reactions

Maria I. Lapuh et al.

Summary: This work describes a novel two-step domino photochemical reaction that allows straightforward access to a variety of thietane derivatives. The reaction involves the generation of unprecedented thiocarbonyl intermediates from stable phenacyl sulfides, which then react with diverse electron-deficient alkene partners to form the thietane core. The regio- and diastereoselectivity of this [2+2] photocycloaddition has been rationalized and controlled for many substrates.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Katie A. Rykaczewski et al.

Summary: In this work, a scalable synthesis method for various azetidine compounds with different properties was developed, and their potential applications in the field of high-energy materials were explored. The synthesized compounds, prepared through a visible-light-mediated reaction, exhibited excellent performance and physical properties, making them promising candidates for novel solid melt-castable explosive materials and liquid propellant plasticizers. This study demonstrates the feasibility of the visible-light synthesis method and highlights the influence of stereochemistry on the physical properties of azetidine-based energetics.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Visible light-mediated synthesis of α-alkoxy/hydroxy diarylacetaldehydes from terminal alkynes

Jaswant Kumar et al.

Summary: This study presents a visible light-mediated approach for the one-step synthesis of alpha-alkoxy/hydroxy diarylacetaldehydes using alcohols as nucleophiles. The method involves the oxidative coupling of alkynes with benzoquinone and alcohols at room temperature, enabling the construction of a highly functionalized quaternary center. The use of copper(I) cyanide as a catalyst increases the electrophilicity of in situ generated p-quinone methides, allowing alcohols to act as nucleophiles. This mild and simple protocol shows no discrimination between aliphatic and aromatic alkynes as coupling partners.

NEW JOURNAL OF CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Enantioselective, Visible Light Mediated Aza Paterno-Buchi Reactions of Quinoxalinones

Xinyao Li et al.

Summary: 3-Substituted quinoxalin-2(1H)-ones and various aryl-substituted or tethered olefins can undergo an enantioselective aza Paterno-Buchi reaction upon irradiation with a chiral sensitizer at lambda=420 nm. The absolute and relative configuration of the products were elucidated by X-ray crystallography, suggesting triplet energy transfer in a hydrogen-bonded complex between the imine substrate and the catalyst. Preliminary experiments also explored intramolecular cycloaddition and alternative reaction modes of quinoxalinones.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Highly Efficient Iridium-Based Photosensitizers for Thia-Paterno-Buchi Reaction and Aza-Photocyclization

Jian He et al.

Summary: Substrates in excited state differ significantly from the corresponding ground state, making photocatalytic systems increasingly popular for activation of substrates. By optimizing the properties of photosensitizers, a series of iridium complexes with high performance were successfully designed for various challenging photocycloaddition reactions.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

1-and 2-Azetines via Visible Light-Mediated [2+2]-Cycloadditions of Alkynes and Oximes

Emily R. Wearing et al.

Summary: A visible light-mediated approach for the synthesis of azetines, including 1- and 2-azetines, has been reported in this study. The method utilizes the unique triplet state reactivity of oximes, specifically 2-isoxazolines, and commercially available iridium photocatalyst for the formation of 2-azetines through intermolecular [2 + 2]-cycloaddition. Selective formation of 1-azetines occurs through a second consecutive energy transfer process and subsequent N-O bond homolysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Multidisciplinary

Taming the excited state reactivity of imines - from non-radiative decay to aza Paterno-Buchi reaction

Sunil Kumar Kandappa et al.

Summary: This review discusses the excited state characteristics of imines and the processes governing their photochemical and photophysical properties, as well as pathways for deactivation and types of photochemical reactions. It also highlights recent strategies developed to address fundamental issues in the aza Paterno-Buchi reaction.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Organic

[2+2] Photochemical Cycloaddition in Organic Synthesis

Debayan Sarkar et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Visible-Light-Driven [2+2] Photocycloadditions between Benzophenone and C=C Bonds in Unsaturated Lipids

Hai-Fang Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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)

Review Chemistry, Organic

Recent synthesis of thietanes

Jiaxi Xu

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Triplet Energy Transfer Photocatalysis: Unlocking the Next Level

Felix Strieth-Kalthoff et al.

Article Chemistry, Multidisciplinary

Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions

Marc R. Becker et al.

NATURE CHEMISTRY (2020)

Article Chemistry, Organic

Microfluidic Visible-Light Paterno-Buchi Reaction of Oxindole Enol Ethers

Pietro Franceschi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Synthesis of azetidines by aza Paterno-Buchi reactions

Alistair D. Richardson et al.

CHEMICAL SCIENCE (2020)

Review Chemistry, Multidisciplinary

Visible-Light-Induced Organic Photochemical Reactions through Energy-Transfer Pathways

Quan-Quan Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Intermolecular 2+2 Carbonyl-Olefin Photocycloadditions Enabled by Cu(I)-Norbornene MLCT

Daniel M. Flores et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Multidisciplinary Sciences

Functionalized azetidines via visible light-enabled aza Paterno-Buchi reactions

Marc R. Becker et al.

NATURE COMMUNICATIONS (2019)

Article Biochemistry & Molecular Biology

The Paterno-Buchi reaction - a comprehensive review

Maurizio D'Auria

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES (2019)

Review Chemistry, Multidisciplinary

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

Leyre Marzo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes

Simone Stegbauer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Energy transfer catalysis mediated by visible light: principles, applications, directions

Felix Strieth-Kalthoff et al.

CHEMICAL SOCIETY REVIEWS (2018)

Review Chemistry, Physical

The Paterno-Buchi reaction-Mechanisms and application to organic synthesis

Maxime Freneau et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Synthesis of a Bicyclic Azetidine with In Vivo Antimalarial Activity Enabled by Stereospecific, Directed C(sp3)-H Arylation

Micah Maetani et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Realizing an Aza Paterno-Buchi Reaction

Elango Kumarasamy et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

James A. Bull et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Organic

Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione

Dong-Dong Wu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Article Chemistry, Organic

Synthesis of thietane nucleoside with an anomeric hydroxymethyl group

Naozumi Nishizono et al.

TETRAHEDRON (2011)

Review Chemistry, Multidisciplinary

Oxetanes as Versatile Elements in Drug Discovery and Synthesis

Johannes A. Burkhard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Chemistry, Medicinal

Triazole oxytocin antagonists: Identification of an aryloxyazetidine replacement for a biaryl substituent

Alan Brown et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2010)

Article Chemistry, Multidisciplinary

Visible light photocatalysis as a greener approach to photochemical synthesis

Tehshik P. Yoon et al.

NATURE CHEMISTRY (2010)

Article Chemistry, Medicinal

7-Sulfonamido-3-benzazepines as potent and selective 5-HT2C receptor agonists: Hit-to-lead optimization

Paul V. Fish et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2009)

Review Chemistry, Multidisciplinary

Photocatalysis. A multi-faceted concept for green chemistry

Davide Ravelli et al.

CHEMICAL SOCIETY REVIEWS (2009)

Article Chemistry, Multidisciplinary

New 6-oxa-2-silabicyclo[2.2.0]hexanes by photochemical conversion of acyl(allyl)(dimethyl) silanes

Catherine Hammaecher et al.

CHEMICAL COMMUNICATIONS (2008)

Review Chemistry, Multidisciplinary

Glossary of terms used in Photochemistry 3(rd) Edition (IUPAC Recommendations 2006)

S. E. Braslavsky

PURE AND APPLIED CHEMISTRY (2007)

Article Chemistry, Organic

Photoinduced [2 epsilon+epsilon 2] cycloadditions (the Paterno-Buchi reaction) of 1H-1-acetylindole-2,3-dione with alkenes

J Xue et al.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (2001)

Article Chemistry, Organic

Photoinduced reactions of 1-acetylisatin with phenylacetylenes

J Xue et al.

ORGANIC LETTERS (2000)