Themed collection Most popular 2022 organic chemistry articles
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Umpolung strategies for the functionalization of peptides and proteins
This perspective highlights the growing body of literature that leverages polarity reversal (umpolung reactivity) for the selective modification of proteinogenic functionalities and identifies opportunities for further innovation.
Chem. Sci., 2022,13, 2809-2823
https://doi.org/10.1039/D1SC06133J
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Photocatalytic C(sp3) radical generation via C–H, C–C, and C–X bond cleavage
C(sp3) radicals (R˙) are of broad research interest and synthetic utility.
Chem. Sci., 2022,13, 5465-5504
https://doi.org/10.1039/D2SC00202G
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H-bond cooperativity: polarisation effects on secondary amides
Formation of an intramolecular phenol-amide H-bond leads to a dramatic increase in the H-bond donor strength of the amide NH group. Polarisation of the amide group is directly proportional to the polarity of the phenol H-bond donor.
Chem. Sci., 2022,13, 11863-11868
https://doi.org/10.1039/D2SC04271A
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Fast relaxing red and near-IR switchable azobenzenes with chalcogen and halogen substituents: periodic trends, tuneable thermal half-lives and chalcogen bonding
The synthesis of red-shifted azobenzenes functionalised with heavy chalcogen and halogen substituents is reported, enabling photo-switching with red and near IR light and Z → E thermal isomerization rates spanning seven orders of magnitude.
Chem. Sci., 2022,13, 11551-11559
https://doi.org/10.1039/D2SC04601F
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BQ-AurIPr: a redox-active anticancer Au(I) complex that induces immunogenic cell death
A redox-active anticancer Au(I) complex that induces immunogenic cell death in non-small cell lung cancer cells has been identified. Mitochondrial oxidative stress leading to mitophagy-dependent secretion of various DAMPs is implicated as the main mechanism inducing ICD.
Chem. Sci., 2022,13, 10779-10785
https://doi.org/10.1039/D2SC03756D
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Discovery of novel drug-like antitubercular hits targeting the MEP pathway enzyme DXPS by strategic application of ligand-based virtual screening
We identified two drug-like antitubercular hits with submicromolar inhibition constants against the target 1-deoxy-D-xylulose-5-phosphate synthase (DXPS) with a new mode of action and promising activity against drug-resistant tuberculosis.
Chem. Sci., 2022,13, 10686-10698
https://doi.org/10.1039/D2SC02371G
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Highly contorted superhelicene hits near-infrared circularly polarized luminescence
This twisted superhelicene employed its twists and loops to shine chiral emission into the NIR region. The proof of its promising applicability in optoelectronic devices is the analogous chiroptical properties obtained in solution and thin films.
Chem. Sci., 2022,13, 10267-10272
https://doi.org/10.1039/D2SC03452B
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Ferroptosis promotes sonodynamic therapy: a platinum(II)–indocyanine sonosensitizer
A novel platinum(II)–cyanine complex showed a greater excellent sonodynamic therapeutic effect than photodynamic therapy in vivo. This work expands the biological applications of metal complexes from traditional photodynamic therapy to sonodynamic therapy.
Chem. Sci., 2022,13, 9921-9926
https://doi.org/10.1039/D2SC02597C
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Non-directed Pd-catalysed electrooxidative olefination of arenes
The Fujiwara–Moritani reaction using electric current is a powerful tool for the olefination of arenes by Pd-catalysed C–H activation.
Chem. Sci., 2022,13, 9432-9439
https://doi.org/10.1039/D2SC03288K
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Subphthalocyanine capsules: molecular reactors for photoredox transformations of fullerenes
A photoredox cage built by coordination of two pyridyl-subphthalocyanines to Pd centers has proved versatile and efficient to catalyze photoredox addition reactions over encapsulated C60.
Chem. Sci., 2022,13, 9249-9255
https://doi.org/10.1039/D2SC01931K
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Iridium-catalyzed α-selective deuteration of alcohols
An α-selective, iridium(III)-bipyridonate-catalyzed hydrogen isotope exchange of alcohols using D2O has been developed for the direct, chemoselective deuteration of primary and secondary alcohols, thereby providing deuterated bioactive molecules.
Chem. Sci., 2022,13, 8744-8751
https://doi.org/10.1039/D2SC01805E
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Catalytic defluorinative ketyl–olefin coupling by halogen-atom transfer
A catalytic ketyl–olefin coupling reaction including sequentially orchestrated Lewis acid activation, halogen-atom transfer, radical addition, single-electron reduction and β-fluoro elimination has been developed.
Chem. Sci., 2022,13, 7855-7862
https://doi.org/10.1039/D2SC02732A
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Zn(II)-Coordination-driven self-assembled nanoagents for multimodal imaging-guided photothermal/gene synergistic therapy
siRNA@PT-ZIF-8 was prepared by one pot self-assembly for tri-mode imaging guided mild-temperature photothermal synergetic gene therapy.
Chem. Sci., 2022,13, 7355-7364
https://doi.org/10.1039/D2SC01769E
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General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors.
Chem. Sci., 2022,13, 6512-6518
https://doi.org/10.1039/D2SC01799G
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Customising excitation properties of polycyclic aromatic hydrocarbons by rational positional heteroatom doping: the peri-xanthenoxanthene (PXX) case
In this paper we tackle the challenge of gaining control of the photophysical properties of PAHs through a site-specific N-doping within the structural aromatic framework.
Chem. Sci., 2022,13, 6335-6347
https://doi.org/10.1039/D2SC01038K
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A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation
An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters.
Chem. Sci., 2022,13, 5701-5706
https://doi.org/10.1039/D2SC01363K
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A sequential cyclization/π-extension strategy for modular construction of nanographenes enabled by stannole cycloadditions
Stannoles are introduced as a new, spontaneously aromatizing diene for [4 + 2] cycloadditions that can be easily introduced into diverse conjugated systems, facilitating the efficient synthesis of complex PAHs and their π-extension.
Chem. Sci., 2022,13, 5568-5573
https://doi.org/10.1039/D2SC00397J
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Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation
Carboxylic acids can now serve as a single point of entry to several sulfonyl functional groups by a one-step organophotocatalytic sulfonylation, revealing structural effects that enable the photocatalysis.
Chem. Sci., 2022,13, 4170-4179
https://doi.org/10.1039/D2SC00789D
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An integrated platform approach enables discovery of potent, selective and ligand-competitive cyclic peptides targeting the GIP receptor
mRNA display generates vast datasets of protein binders. Bioinformatic clustering of the sequences combined with high throughput synthesis and analysis methods allow efficient prioritisation of hits for in vivo experiments.
Chem. Sci., 2022,13, 3256-3262
https://doi.org/10.1039/D1SC06844J
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NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones
Unprecedented NHC and photocatalysis co-catalyzed radical 1,4-sulfonylacylation of 1,3-enynes has been realized, providing structurally diversified tetrasubstituted allenyl ketones via allenyl and ketyl radical cross-coupling.
Chem. Sci., 2022,13, 3169-3175
https://doi.org/10.1039/D1SC06100C
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Selective covalent targeting of SARS-CoV-2 main protease by enantiopure chlorofluoroacetamide
Chlorofluoroacetamide (CFA) was used as the warhead for covalent targeting of SARS-CoV-2 Mpro. The chirality at CFA showed marked influence on inhibitory activity, suggesting stereospecific activation of CFA for cysteine modification in the protein.
Chem. Sci., 2022,13, 3027-3034
https://doi.org/10.1039/D1SC06596C
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Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations
Despite indisputable progress in the development of electrochemical transformations, electrocatalytic annulations for the synthesis of biologically relevant three-dimensional spirocyclic compounds has as of yet not been accomplished.
Chem. Sci., 2022,13, 2783-2788
https://doi.org/10.1039/D1SC07124F
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Pressing matter: why are ionic liquids so viscous?
We use an experimental approach to compare an ionic liquid with a molecular mimic, focusing on viscosities. Charge network and coulombic compaction contribute significantly to the high viscosity of ionic liquids; we discuss the implications on their design and optimisation.
Chem. Sci., 2022,13, 2735-2743
https://doi.org/10.1039/D1SC06857A
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Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis
An acylative Suzuki-type cross-coupling of alkyl trifluoroborates and acid fluorides was developed by merging NHC organocatalysis with photoredox catalysis. A broad spectrum of ketones could be facilely synthesised under mild reaction conditions.
Chem. Sci., 2022,13, 2584-2590
https://doi.org/10.1039/D1SC06102J
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Retaining the structural integrity of disulfide bonds in diphtheria toxoid carrier protein is crucial for the effectiveness of glycoconjugate vaccine candidates
The introduction of glycoconjugate vaccines marks an important point in the fight against various infectious diseases.
Chem. Sci., 2022,13, 2440-2449
https://doi.org/10.1039/D1SC01928G
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Prediction of protein pKa with representation learning
We developed new empirical ML model for protein pKa prediction with MAEs below 0.5 for all amino acid types.
Chem. Sci., 2022,13, 2462-2474
https://doi.org/10.1039/D1SC05610G
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Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties
An enhanced N-directed electrophilic C–H borylation methodology has been developed that provides access to azaborine containing helicenes.
Chem. Sci., 2022,13, 1136-1145
https://doi.org/10.1039/D1SC06513K
About this collection
This specially curated collection pulls together some of the most popular articles from 2022 in the field of organic chemistry. The collection presents some outstanding contributions to the field, ranging from photocatalytic radical generation to prediction of protein pKa, 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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