Synthesis of 2-Fluorobenzofuran by Photocatalytic Defluorinative Coupling and 5-endo-trig Cyclization

Review Chemistry, Applied

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

Feng Zhao et al.

Summary: This review summarizes the recent developments of new methods for the synthesis of difluoromethyl motifs or difluoroalkenes from trifluoromethylated aromatic compounds or trifluoromethyl alkenes via single C(sp(3))-F bond cleavage.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Review Chemistry, Medicinal

Therapeutic Potential of Naturally Occurring Benzofuran Derivatives and Hybrids of Benzofurans with other Pharmacophores as Antibacterial Agents

Zhi Xu et al.

Summary: Gram-positive and Gram-negative pathogens pose a significant threat to human health, resulting in severe diseases and high mortality rates. Developing novel antibacterial agents remains challenging due to the emergence of more virulent and drug-resistant pathogens. Benzofuran, with its diverse pharmacological activities, shows promise as a potential scaffold for discovering new antibacterial agents. This review focuses on the recent advancements in naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents, providing valuable insights into their chemical structures and structure-activity relationships.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2022)

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Article Chemistry, Medicinal

A Close-up Look at the Chemical Space of Commercially Available Building Blocks for Medicinal Chemistry

Yuliana Zabolotna et al.

Summary: Efficient synthesis of desired compounds is crucial for chemical space exploration in drug discovery, which is influenced by both established synthetic protocols and the availability of corresponding building blocks (BBs). This study analyzes the chemical space of 400,000 purchasable BBs, examining their physicochemical properties and diversity to assess their coverage of medicinal chemistry needs. The analysis is based on a universal topographic map that visualizes libraries and their differences in coverage.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2022)

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Article Chemistry, Multidisciplinary

C-F bond functionalizations of trifluoromethyl groups via radical intermediates

Tesfaye Tebeka Simur et al.

Summary: This review article provides a brief overview of recently reported methods used to functionalize C-F bonds in CF3 groups via radical intermediates, with an emphasis on the discussion of mechanistic aspects and synthetic applications.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Synthesis of 5-Fluoro-dihydroindolizines from Pyrrole-2-acetic Acidsand Trifluoromethyl Alkenes via Dual C-F Bond Cleavage in a CF3 Group

Zhengchang Sun et al.

Summary: In this study, we describe the synthesis of 5-fluoro-dihydroindolizines through dual C-F bond cleavage in a trifluoromethyl group. The first C-F bond is cleaved via photocatalytic defluorinative coupling, resulting in gem-difluoroalkenes bearing an unprotected pyrrole motif. Subsequently, an intramolecular SNV reaction closes the ring by forming a C-N bond concomitantly with the cleavage of the second C-F bond. The reactions also allow the assembly of 6-fluoro-dihydropyrido[1,2-a]indoles using indole-2-acetic acids as substrates.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Selective C-F Bond Etherification of Trifluoromethylalkenes with Phenols

Qingqiang Tian et al.

Summary: A novel protocol for selective C-F bond etherification of trifluoromethylalkenes and phenols has been reported, generating the pharmaceutically privileged difluoromethylene moiety. DFT calculation results and control experiments suggest the involvement of metal ion Cs+ in the defluorooxylation process. Furthermore, the obtained product exhibits good insecticidal activity.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Self-Sustaining Fluorination of Active Methylene Compounds and High-Yielding Fluorination of Highly Basic Aryl and Alkenyl Lithium Species with a Sterically Hindered N-Fluorosulfonamide Reagent

Yuhao Yang et al.

Summary: A novel N-fluorosulfonamide reagent NFBB was developed for the high-yielding fluorination of active methylene compounds and the synthesis of highly basic (hetero)aryl and alkenyl compounds with unprecedented high or quantitative yields.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Applied

Photoinduced Ligand-to-Metal Charge Transfer of Carboxylates: Decarboxylative Functionalizations, Lactonizations, and Rearrangements

Sigrid Gavelle et al.

Summary: This article provides an overview of recent advances in LMCT of carboxylates, with a special focus on mechanistic aspects of these transformations. Carboxylic acids can be considered as ideal biobased feedstocks in sustainable processes, and the photoinduced ligand-to-metal charge transfer offers low-consuming energy source and innovative conditions for mild and highly selective functionalization.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Review Biochemistry & Molecular Biology

Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

Lei Zhou

Summary: By utilizing visible light photoredox catalysis, researchers are able to cleave C-F bonds and prepare valuable partially fluorinated products. This method is milder, easier to handle, and environmentally friendly compared to conventional C-F bond formation methods.

MOLECULES (2021)

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Review Chemistry, Applied

Visible Light Assisted Radical-Polar/Polar-Radical Crossover Reactions in Organic Synthesis

Shivani Sharma et al.

Summary: The novel concept of radical-polar crossover (RPCO) and polar-radical crossover (PRCO) reactions has emerged in recent years as a valuable tool bridging the gap between polar and radical reactions, overcoming their limitations, and improving the green quotient of reactions. The development and transformation of this area into synthetically important reactions is summarized in this review.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Radical philicity and its role in selective organic transformations

Faeze Parsaee et al.

Summary: Radical philicity, the ability of radicals to act as nucleophiles or electrophiles, is an important concept in organic chemistry. Traditionally, radicals are considered electron deficient, but the term "electron deficient" can imply electrophilicity in modern literature. This discrepancy has led to misconceptions about radical behavior, as many radicals actually exhibit nucleophilic behavior. This review aims to guide the understanding and prediction of radical philicity, demonstrating that not all radicals behave as electrophiles.

NATURE REVIEWS CHEMISTRY (2021)

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Review Chemistry, Organic

Recent advance in the C-F bond functionalization of trifluoromethyl-containing compounds

Guobing Yan et al.

Summary: Activation of C-F bonds in trifluoromethyl-containing compounds is a challenging task in organic synthesis, with significant progress being made in the past decades mainly involving trifluoromethylalkenes, trifluoromethylated aromatic and alkyl compounds, among others.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Multidisciplinary