Themed collection Most popular 2023 organic chemistry articles

28 items
Open Access Perspective

Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations

By drawing inspiration from photoredox catalysis, the field of radical-mediated alkane functionalization has made remarkable advancements recently to address the challenges of today and future.

Graphical abstract: Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations
Open Access Review Article

Rejuvenation of dearomative cycloaddition reactions via visible light energy transfer catalysis

Dearomative cycloaddition is a powerful technique to access sp3-rich three-dimensional structural motifs from simple flat, aromatic feedstock.

Graphical abstract: Rejuvenation of dearomative cycloaddition reactions via visible light energy transfer catalysis
Open Access Review Article

A field guide to flow chemistry for synthetic organic chemists

This review explores the benefits of flow chemistry and dispels the notion that it is a mysterious “black box”, demonstrating how it can push the boundaries of organic synthesis through the understanding of its governing principles.

Graphical abstract: A field guide to flow chemistry for synthetic organic chemists
Open Access Edge Article

Regioselective ortho halogenation of N-aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C–halogen bond installation

We report the discovery of an ortho regioselective oxidative halodeboronation of N-aryl amides and ureas with wide-ranging applications in pharmaceuticals, materials science, and synthetic organic chemistry.

Graphical abstract: Regioselective ortho halogenation of N-aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C–halogen bond installation
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group

Benzoyldiisopropylchlorosilane (BDIPSCl), an acylchlorosilane that represents a new class of acylsilanes, is introduced as a new visible light photocleavable silicon-based alcohol protecting group.

Graphical abstract: Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Trifluoromethylarylation of alkenes using anilines

This work unlocks the use of anilines in the selective trifluoromethylarylation of olefins via a mild protocol that avoids transition metals, expensive photocatalysts and additives, where hexafluoroisopropanol is a unique solvent that promotes it.

Graphical abstract: Trifluoromethylarylation of alkenes using anilines
From the themed collection: #MyFirstChemSci 2023
Open Access Edge Article

Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

An intriguing chiral phosphoric acid-catalyzed asymmetric hydrolytic ring-opening of racemic aziridines via regiodivergent PKR is presented, providing an efficient approach for the construction of chiral β-amino alcohols.

Graphical abstract: Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Photocatalytic redox-neutral selective single C(sp3)–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Site-selective and direct C–F bond functionalization of polyfluorinated iminosulfides was achieved to synthesize 3-fluoro-3-perfluoroalkyl-γ-lactams under photoredox-neutral conditions.

Graphical abstract: Photocatalytic redox-neutral selective single C(sp3)–F bond activation of perfluoroalkyl iminosulfides with alkenes and water
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

We have developed a divergent approach for the catalytic asymmetric synthesis of skeletally different benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans. The methodology involves sequential catalysis: chiral H-bonding catalysis and Lewis base catalysis.

Graphical abstract: Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis

Carboxylic acids can be converted directly to bioisosteric 3-oxetanols by leveraging the unique reactivity of photoredox catalysis. Cr-mediated and Cr-free variants of the reaction have been developed, both having quantum yields greater than 5.

Graphical abstract: Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Azido-alkynylation of alkenes through radical-polar crossover

An azido-alkynylation of alkenes has been developed by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. This method allows the synthesis of homopropargylic azides, which could be transformed into pyrroles or bioactive amines.

Graphical abstract: Azido-alkynylation of alkenes through radical-polar crossover
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Chiral gem-difluoroalkyl reagents: gem-difluoroalkyl propargylic borons and gem-difluoroalkyl α-allenols

Two types of chiral gem-difluoroalkyl reagents, chiral gem-difluoroalkyl propargylic borons and gem-difluoroalkyl α-allenols were developed by means of Rh-catalyzed enantioselective B–H bond insertion and Lewis acid-promoted allenylation.

Graphical abstract: Chiral gem-difluoroalkyl reagents: gem-difluoroalkyl propargylic borons and gem-difluoroalkyl α-allenols
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Direct mechanocatalysis by resonant acoustic mixing (RAM)

We demonstrate a simple strategy to use a metal surface to directly catalyse mechanochemical reactions by Resonant Acoustic Mixing (RAM), a scalable mechanochemical methodology that uniquely eliminates the need for grinding media or bulk solvent.

Graphical abstract: Direct mechanocatalysis by resonant acoustic mixing (RAM)
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Cobalt-catalyzed enantioselective C–H/N–H annulation of aryl sulfonamides with allenes or alkynes: facile access to C–N axially chiral sultams

A cobalt-catalyzed atroposelective C–H/N–H annulation of sulfonamides with allenes or alkynes, using either chemical or electrochemical oxidation, was disclosed, which affords C–N axially chiral sultams with high regio- and enantio-selectivities.

Graphical abstract: Cobalt-catalyzed enantioselective C–H/N–H annulation of aryl sulfonamides with allenes or alkynes: facile access to C–N axially chiral sultams
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Photoredox radical/polar crossover enables C–H gem-difunctionalization of 1,3-benzodioxoles for the synthesis of monofluorocyclohexenes

A sequential C–H gem-difunctionalization of 1,3-benzodioxoles with α-trifluoromethyl alkenes and electron-deficient alkenes in a redox-neutral radical polar crossover manifold have been developed for the synthesis of monofluorocyclohexenes.

Graphical abstract: Photoredox radical/polar crossover enables C–H gem-difunctionalization of 1,3-benzodioxoles for the synthesis of monofluorocyclohexenes
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes

EDA complexes with catalytic triarylamines allow C–H perfluoroalkylation of arenes and heteroarenes under visible light irradiation in pH- and redox-neutral conditions. A detailed photophysical characterization of the EDA complex is provided.

Graphical abstract: Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green

Technology for generating especially important amide and peptide bonds from carboxylic acids and amines that avoids traditional coupling reagents is described.

Graphical abstract: Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Nitrogen atom insertion into indenes to access isoquinolines

We report a convenient protocol for a nitrogen atom insertion into indenes to afford isoquinolines. The strategy further enables the synthesis of pyridines from cyclopentadienes and a facile access to 15N labelled isoquinolines.

Graphical abstract: Nitrogen atom insertion into indenes to access isoquinolines
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

1-Azahomocubane

1-Azahomocubane has been prepared 56 years after the parent hydrocarbon. Introduction of a nitrogen atom into this constrained polycyclic environment resulted in minimal changes to the framework geometry, with s-character of the nitrogen lone pair increasing due to strain.

Graphical abstract: 1-Azahomocubane
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

The development of strategies for single and selective C–F bond activation represents an important avenue to overcome limitations in the synthesis of valuable fluorine-containing compounds.

Graphical abstract: Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Unveiling a new aspect of oxocarbons: open-shell character of 4- and 5-membered oxocarbon derivatives showing near-infrared absorption

Near-infrared absorbing oxocarbon derivatives, so-called squaraine and croconaine dyes, regarded as closed-shell species so far, display the intermediate open-shell character that impacts their one- and two-photon absorption properties.

Graphical abstract: Unveiling a new aspect of oxocarbons: open-shell character of 4- and 5-membered oxocarbon derivatives showing near-infrared absorption
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Deaminative coupling of benzylamines and arylboronic acids

A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported.

Graphical abstract: Deaminative coupling of benzylamines and arylboronic acids
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles

A novel photoinduced heteroarylation route to substituted oxindoles is disclosed.

Graphical abstract: Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Visible-light-induced organocatalytic enantioselective N–H insertion of α-diazoesters enabled by indirect free carbene capture

It has been a long-standing challenge to achieve catalytic asymmetric X–H bond insertion with free carbenes. Herein, an indirect visible-light-promoted asymmetric N–H insertion is disclosed.

Graphical abstract: Visible-light-induced organocatalytic enantioselective N–H insertion of α-diazoesters enabled by indirect free carbene capture
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Photochemical halogen-bonding assisted generation of vinyl and sulfur-centered radicals: stereoselective catalyst-free C(sp2)–S bond forming reactions

Constructing alkenyl sulfides has never been so easy! A new halogen-bonding assisted photochemical transformation allows for the catalyst free cross-coupling between vinyl halides and thiols under basic conditions and visible light irradiation.

Graphical abstract: Photochemical halogen-bonding assisted generation of vinyl and sulfur-centered radicals: stereoselective catalyst-free C(sp2)–S bond forming reactions
From the themed collection: #RSCPoster Twitter Conference
Open Access Edge Article

Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry

Proof of concept enantioselective transformation via photoelectrocatalysis was reported on Cu-catalyzed enantioselective decarboxylative cyanation, which features mild conditions, high enantioselectivity and a reasonable range of functionalities.

Graphical abstract: Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry
From the themed collection: Most popular 2023 organic chemistry articles
Open Access Edge Article

Mechanochemical protocol facilitates the generation of arylmanganese nucleophiles from unactivated manganese metal

A ball-milling approach allows the efficient activation of unactivated manganese metal and thus makes the direct generation of arylmanganese nucleophiles feasible without the need for complicated pre-activation processes and metal additives.

Graphical abstract: Mechanochemical protocol facilitates the generation of arylmanganese nucleophiles from unactivated manganese metal
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Cobalt-electrocatalytic C–H hydroxyalkylation of N-heteroarenes with trifluoromethyl ketones

By merging paired electrolysis and cobalt catalysis, we have developed an electrochemical redox-neutral coupling for the synthesis of N-heteroaryl trifluoromethyl carbinols from readily available N-heteroarenes and trifluoromethyl ketones.

Graphical abstract: Cobalt-electrocatalytic C–H hydroxyalkylation of N-heteroarenes with trifluoromethyl ketones
From the themed collection: Most popular 2023 organic chemistry articles
28 items

About this collection

This specially curated collection pulls together some of the most popular articles from 2023 in the field of organic chemistry. The collection presents some outstanding contributions to the field, ranging from enantioselective photocatalysis to flow chemistry, and as with all Chemical Science articles – they are all completely free to access and read. We hope you enjoy browsing through this collection.

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