Themed collection Most popular 2024 organic chemistry articles


Detour to success: photoswitching via indirect excitation
Photoswitching via indirect excitation allows harnessing low-energy photons to control molecular configuration. Herein, the state of the art of the predominant indirect photoswitching methods is presented.
Chem. Sci., 2024,15, 11684-11698
https://doi.org/10.1039/D4SC02538E

The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions
Initial calculations of environmental footprints associated with using Ni vs Pd catalysis in a representative metal-catalyzed Suzuki–Miyaura cross-coupling reveal that the choice of ligated metal is often NOT of consequence. Rather, it is a culmination of other parameters such as medium.
Chem. Sci., 2024,15, 9016-9025
https://doi.org/10.1039/D4SC00482E

Continuous flow synthesis enabling reaction discovery
This Perspective article highlights recent studies in which continuous flow approaches exploiting photochemical, electrochemical, and thermal reactions led to the discovery and subsequent exploitation of new reactions and reactivity patterns.
Chem. Sci., 2024,15, 4618-4630
https://doi.org/10.1039/D3SC06808K

Biocompatible strategies for peptide macrocyclisation
The identification of macrocyclic peptides in drug discovery demands not only advanced screening strategies but also robust and reliable synthetic methodologies to constrain peptides under biocompatible conditions.
Chem. Sci., 2024,15, 2300-2322
https://doi.org/10.1039/D3SC05738K

Diaryl hypervalent bromines and chlorines: synthesis, structures and reactivities
Diaryl hypervalent bromines and chlorines emerge as a novel foundation for advancing organic chemistry. This article provides an overview of the synthetic methodology, structural variations, and the latest transformations unearthed in this context.
Chem. Sci., 2024,15, 1557-1569
https://doi.org/10.1039/D3SC05382B

Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations
Green oxidation reactions performed by organocatalytic activation of hydrogen peroxide.
Chem. Sci., 2024,15, 1177-1203
https://doi.org/10.1039/D3SC05618J

Improved transition metal photosensitizers to drive advances in photocatalysis
This perspective focuses on strategies to manipulate and optimize three key determinants of metal-based molecular photosensitizers – the absorption profile, the excited-state redox potentials, and the excited-state lifetime.
Chem. Sci., 2024,15, 77-94
https://doi.org/10.1039/D3SC04580C

Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry
This review article highlights the diverse ways in which recent developments in the areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry.
Chem. Sci., 2024,15, 1204-1236
https://doi.org/10.1039/D3SC05400D

Structural constraint at a P–P bond: phosphinophosphination of alkenes, alkynes, and carbonyls by a concerted mechanism
A structural constraint approach at a P–P bond is presented that enables the phosphinophosphination of alkynes, alkenes, and carbonyls with high regio- and diastereoselectivity. The apolar nature of the P–P bond facilitates a concerted mechanism.
Chem. Sci., 2025,16, 1716-1721
https://doi.org/10.1039/D4SC06581F

Bridge editing of spin-flip emitters gives insight into excited state energies and dynamics
The bridge X of the chelate ligand modifies doublet and quartet state energies and the excited state dynamics of luminescent chromium(III) complexes.
Chem. Sci., 2024,15, 20251-20262
https://doi.org/10.1039/D4SC05860G

Modular synthesis of α-branched secondary alkylamines via visible-light-mediated carbonyl alkylative amination
A multicomponent method for the synthesis of α-branched secondary alkylamines is described. The method provides expedited access to saturated N-heterocycles, and enables selective alkylation of primary amines over cyclic secondary amines.
Chem. Sci., 2024,15, 14888-14898
https://doi.org/10.1039/D4SC03916E

Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes
A novel palladium-catalyzed strategy was employed to achieve higher-order (4 + 3) cycloadditions of bicyclobutanes with various 2-alkylidenetrimethylene carbonates to synthesize 2-oxabicyclo[4.1.1]octanes.
Chem. Sci., 2024,15, 13942-13948
https://doi.org/10.1039/D4SC02998D

Fast photochromism of helicene-bridged imidazole dimers
The unique optical and magnetic properties of organic biradicaloids on polycyclic aromatic hydrocarbons are of fundamental interest in the development of novel organic optoelectronic materials.
Chem. Sci., 2024,15, 13343-13350
https://doi.org/10.1039/D4SC03578J

Chemo-, regio-, and stereoselective tetrafunctionalization of fluoroalkynes enables divergent synthesis of 5-7-membered azacycles
A 1,2,3,4-tetrafunctionalization of polyfluoroalkynes for the divergent construction of 5-7-membered (E)-1,2-difluorovinyl azacycles is developed.
Chem. Sci., 2024,15, 12026-12035
https://doi.org/10.1039/D4SC03230F

Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes
Bicyclo[4.1.1]octanes (BCOs) were synthesized in up to quantitative yields through the formal [4+2] cycloaddition of aryl and alkyl bicyclobutane (BCB) ketones with dienol silyl ethers using Al(OTf)3 as a Lewis acid catalyst.
Chem. Sci., 2024,15, 10823-10829
https://doi.org/10.1039/D4SC02767A

Acridine photocatalysis enables tricomponent direct decarboxylative amine construction
Diverse amines and amino acids are now readily accessed from carboxylic acids, aldehydes, and amine precursors in a direct decarboxylative reaction enabled by a homogeneous triple catalytic system based on acridine photocatalysis.
Chem. Sci., 2024,15, 9582-9590
https://doi.org/10.1039/D4SC02356K

An anthropocene-framed transdisciplinary dialog at the chemistry-energy nexus
Five molecules at the energy-chemistry nexus, their position in the planetary boundary framework and Anthropocene-spurred interdisciplinary connections between chemistry, social sciences, and humanities to help define sustainability-driven research.
Chem. Sci., 2024,15, 9054-9086
https://doi.org/10.1039/D4SC00099D

Aromatization-driven deconstructive functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis
The aromatization-driven deconstructive coupling of spiro carbocycles with organic halides via dual photoredox/nickel catalysis is developed. An in-depth mechanism study revealed that this reaction proceeded via a radical-metal crossover pathway.
Chem. Sci., 2024,15, 8993-8999
https://doi.org/10.1039/D4SC01111B

Photoinduced C–H arylation of 1,3-azoles via copper/photoredox dual catalysis
The photo-induced azole C–H arylation was realized with a dual-catalytic copper-based system. Exceedingly mild reaction conditions at ambient temperature and visible light irradiation enabled a broad scope with high functional group tolerance.
Chem. Sci., 2024,15, 7293-7299
https://doi.org/10.1039/D4SC00393D

Iodoarene-directed photoredox β-C(sp3)–H arylation of 1-(o-iodoaryl)alkan-1-ones with cyanoarenes via halogen atom transfer and hydrogen atom transfer
Radical-mediated direct photoredox β-C(sp3)–H arylation of 1-(o-iodoaryl)alkan-1-ones with cyanoarenes directed by an iodoarene group is depicted.
Chem. Sci., 2024,15, 6522-6529
https://doi.org/10.1039/D3SC06637A

Visible-light-driven alkene dicarboxylation with formate and CO2 under mild conditions
Low-cost formate salt was used as the reductant and part of the carboxyl source in a visible-light-driven dicarboxylation of diverse alkenes, including simple styrenes.
Chem. Sci., 2024,15, 6178-6183
https://doi.org/10.1039/D3SC04431A

From propenolysis to enyne metathesis: tools for expedited assembly of 4a,8a-azaboranaphthalene and extended polycycles with embedded BN
A new integrated approach to BN-polycycles is rooted in a clean condensation of amines with B(allyl)3. The end game includes a gram-scale synthesis of BN-naphthalene through efficient aromatization, or assembly of BN-polycycles via enyne metathesis.
Chem. Sci., 2024,15, 5674-5680
https://doi.org/10.1039/D3SC06676B

Chemical and linguistic considerations for encoding Chinese characters: an embodiment using chain-end degradable sequence-defined oligourethanes created by consecutive solid phase click chemistry
The information (a proverb from The Analects of Confucius) is stored in chain-end degradable sequence-defined oligourethanes, sequenced with liquid chromatography-mass spectrometry (LC-MS) under suitable conditions and decrypted with in-house Python scripts.
Chem. Sci., 2024,15, 5284-5293
https://doi.org/10.1039/D3SC06189B

Synthesis of axially chiral diaryl ethers via NHC-catalyzed atroposelective esterification
We present NHC-catalyzed atroposelective esterification of prochiral dialdehydes, delivering enantioenriched axially chiral diaryl ethers. Matched kinetic resolutions amplify the enantioselectivity by removing minor enantiomers via over-functionalization.
Chem. Sci., 2024,15, 4564-4570
https://doi.org/10.1039/D3SC06444A

Mechanochemistry enabling highly efficient Birch reduction using sodium lumps and D-(+)-glucose
In this study, a mechanochemical protocol for highly efficient and ammonia-free sodium-based Birch reduction was developed, leveraging the use of cheap and easy-to-handle sodium lumps and D-(+)-glucose as a proton source.
Chem. Sci., 2024,15, 4452-4457
https://doi.org/10.1039/D3SC06052G

Modular synthesis of functional libraries by accelerated SuFEx click chemistry
The Accelerated SuFEx Click Chemistry (ASCC) protocol, adapted to a 96-well plate format, has been applied to the late-stage derivatization of bioactive molecules and array synthesis of anticancer agents, showcasing its potential for drug discovery.
Chem. Sci., 2024,15, 3879-3892
https://doi.org/10.1039/D3SC05729A

Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction
A reductive and denitrative amination of nitroarenes has been developed, allowing the highly selective synthesis of various di- and triarylamines. The protocol employed synthetically upstream nitroarenes as both the electrophiles and amine sources.
Chem. Sci., 2024,15, 3552-3561
https://doi.org/10.1039/D3SC06618E

Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and – lactams
Two complementary strain-enabled radical spirocyclization cascades have been realized to synthesize spirocyclobutyl lactones and – lactams. The reactions operate under mild conditions and demonstrate excellent functional group compatibility.
Chem. Sci., 2024,15, 3182-3191
https://doi.org/10.1039/D3SC05700C

Nitrogen atom insertion into arenols to access benzazepines
Advances in site-selective molecular editing have enabled structural modification on complex molecules.
Chem. Sci., 2024,15, 2612-2617
https://doi.org/10.1039/D3SC05367A

Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid
Herein we report a branch-selective allylation strategy for accessing C2-indolyl-all-carbon quaternary centers using allylboronic acids and implemented this method for the total synthesis of the mersicarpine alkaloid.
Chem. Sci., 2024,15, 1789-1795
https://doi.org/10.1039/D3SC04732F

Photocatalytic, modular difunctionalization of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer
Simple iron salts are able to photocatalyze the diazidation, dichlorination, and fluorochlorination of alkenes via the merger of ligand-to-metal charge transfer (LMCT) and either radical ligand transfer (RLT) or fluorine atom transfer (FAT).
Chem. Sci., 2024,15, 124-133
https://doi.org/10.1039/D3SC05231A
About this collection
This specially curated collection pulls together some of our most popular articles from 2024 in the field of organic chemistry. The collection presents some outstanding contributions to the field, including work on peptide macrocyclisation, coupling reactions, continuous flow synthesis, and much more. As with all Chemical Science articles, this collection is completely free to access and read. We hope you enjoy browsing through this collection!
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