Themed collection Most popular 2023 organic chemistry articles
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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.
Chem. Sci., 2023,14, 6841-6859
https://doi.org/10.1039/D3SC01118F
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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.
Chem. Sci., 2023,14, 12004-12025
https://doi.org/10.1039/D3SC04421A
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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.
Chem. Sci., 2023,14, 4230-4247
https://doi.org/10.1039/D3SC00992K
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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.
Chem. Sci., 2023,14, 13429-13436
https://doi.org/10.1039/D3SC04628A
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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.
Chem. Sci., 2023,14, 12615-12620
https://doi.org/10.1039/D3SC04975B
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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.
Chem. Sci., 2023,14, 12083-12090
https://doi.org/10.1039/D3SC03868H
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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.
Chem. Sci., 2023,14, 12152-12159
https://doi.org/10.1039/D3SC03899H
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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.
Chem. Sci., 2023,14, 11566-11572
https://doi.org/10.1039/D3SC03771A
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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.
Chem. Sci., 2023,14, 10768-10776
https://doi.org/10.1039/D3SC03239F
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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.
Chem. Sci., 2023,14, 10524-10531
https://doi.org/10.1039/D3SC00936J
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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.
Chem. Sci., 2023,14, 9452-9460
https://doi.org/10.1039/D3SC03309K
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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.
Chem. Sci., 2023,14, 9186-9190
https://doi.org/10.1039/D3SC03266C
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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.
Chem. Sci., 2023,14, 7475-7481
https://doi.org/10.1039/D3SC01591B
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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.
Chem. Sci., 2023,14, 7291-7303
https://doi.org/10.1039/D3SC01787G
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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.
Chem. Sci., 2023,14, 6045-6051
https://doi.org/10.1039/D3SC00912B
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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.
Chem. Sci., 2023,14, 3470-3481
https://doi.org/10.1039/D2SC07078B
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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.
Chem. Sci., 2023,14, 3462-3469
https://doi.org/10.1039/D3SC00198A
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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.
Chem. Sci., 2023,14, 2954-2959
https://doi.org/10.1039/D2SC06952K
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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.
Chem. Sci., 2023,14, 2821-2825
https://doi.org/10.1039/D3SC00001J
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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.
Chem. Sci., 2023,14, 2379-2385
https://doi.org/10.1039/D2SC06179A
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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.
Chem. Sci., 2023,14, 1978-1985
https://doi.org/10.1039/D2SC06612B
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Deaminative coupling of benzylamines and arylboronic acids
A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported.
Chem. Sci., 2023,14, 1709-1714
https://doi.org/10.1039/D2SC06055H
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Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles
A novel photoinduced heteroarylation route to substituted oxindoles is disclosed.
Chem. Sci., 2023,14, 897-902
https://doi.org/10.1039/D2SC05918E
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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.
Chem. Sci., 2023,14, 843-848
https://doi.org/10.1039/D2SC05149D
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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.
Chem. Sci., 2023,14, 650-657
https://doi.org/10.1039/D2SC05556B
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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.
Chem. Sci., 2023,14, 705-710
https://doi.org/10.1039/D2SC05428K
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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.
Chem. Sci., 2023,14, 499-505
https://doi.org/10.1039/D2SC05468J
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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.
Chem. Sci., 2023,14, 143-148
https://doi.org/10.1039/D2SC05198B
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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