Themed collection 2024 Organic Chemistry Frontiers HOT articles
![](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/Ajax-GA-Loader.gif)
Direct C(sp2)–H activation of allenes via hydrogen-atom transfer (HAT) in organic synthesis
The highlighted reports demonstrate the unique application of the direct HAT strategy to unlock new reactivity of allenes. With this novel method, a variety of structurally diverse allenes are efficiently workable.
Org. Chem. Front., 2024,11, 2108-2111
https://doi.org/10.1039/D3QO02132G
Cycloparaphenylene-based [2]catenanes: interlocking the carbon nanohoops
In this highlight, recent advances in the design and synthesis of novel cycloparaphenylene (CPP)-based [2]catenanes are presented, with an emphasis on the design strategy and further investigations on their attractive properties.
Org. Chem. Front., 2024,11, 1490-1494
https://doi.org/10.1039/D4QO00033A
Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization
Nickel-catalyzed hydrofunctionalization of π-substrates is a possibly effective method to synthesize several value-added molecular architectures. This review covers the NiH catalyzed hydrofunctionalization reactions of alkenes, alkynes and allenes.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00860J
Precision single-atom editing: new frontiers in nitrogen insertion and substitution for the generation of N-heterocycles
This paper primarily focuses on the editing of nitrogen atoms, encompassing the insertion of N, substitution of C with N, and utilization of 15N in place of 14N for the construction of N-heterocycles.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00812J
Electroreduction Strategy: A Sustainable Tool for Generation of Aryl Radicals
Org. Chem. Front., 2024, Accepted Manuscript
https://doi.org/10.1039/D4QO00846D
Unleashing the potentiality of metals: synergistic catalysis with light and electricity
This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00797B
Catalytic alkane C–H functionalization by carbene insertion into unactivated C(sp3)–H bonds
This review summarizes the developments in the C–H functionalization of saturated hydrocarbons (CnH2n+2 and CnH2n) through catalytic carbene insertion into their C–H bonds dated up to February 2024, based on the categories of the types of carbenes.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00606B
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
Unveiling the beauty of cyclopropane formation: a comprehensive survey of enantioselective Michael initiated ring closure (MIRC) reactions
This review presents a comprehensive overview of the synthesis of cyclopropanes using enantioselective Michael Initiated Ring Closure (MIRC) reactions.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00535J
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products
Oxepanes and thiepanes are central motifs and tenants of many biologically important molecules. This comprehensive review covers synthetic methods for their preparation and use in the total synthesis of polyoxygenated oxepane natural products.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00380B
Site-selective C(sp3)–H functionalization of primary aliphatic amines
C–H bond functionalization represents one of the most efficient and straightforward strategies for diversifying existing molecules.
Org. Chem. Front., 2024,11, 3270-3280
https://doi.org/10.1039/D4QO00324A
Electrochemical switching in mechanically interlocked molecules (MIMs)
Mechanically interlocked molecules (MIMs) which include rotaxanes and catenanes are formed by the mechanical linking of two or more components and has the ability to switch between different states in the presence of an external stimuli.
Org. Chem. Front., 2024,11, 2954-2980
https://doi.org/10.1039/D4QO00061G
Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds
This review summarizes the recent advances (2016–2023) in the stereoselective metal-catalyzed hydrogenation of cyclic α,β-unsaturated ketones, lactams and lactones since considerable developments were made. Where possible the application of these methodologies in synthesis is outlined.
Org. Chem. Front., 2024,11, 2934-2953
https://doi.org/10.1039/D4QO00227J
Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations
The synthesis of small molecules and complex scaffolds is one of the most important topics in organic synthesis.
Org. Chem. Front., 2024,11, 2665-2692
https://doi.org/10.1039/D4QO00396A
Recent progress in the synthesis of N-substituted arylamines by reductive cross-coupling of nitroarenes
This review describes the recent advances in different reaction types and catalytic systems for the construction of C–NAr and S–NAr bonds by nitroaromatic reductive cross-coupling.
Org. Chem. Front., 2024,11, 2638-2664
https://doi.org/10.1039/D4QO00059E
Catalytic intermolecular hydrofunctionalizations of ynamides
This review carefully summarizes the advances achieved in catalytic hydrofunctionalization of ynamides and is categorized by the bond formation type including C−C, C−X, C−O, C−N, C−S, C−P, C−Si, and C−Ge bonds.
Org. Chem. Front., 2024,11, 2351-2374
https://doi.org/10.1039/D4QO00301B
Advancement in the C–H bond alkylation of (hetero)arenes catalyzed by the most abundant transition metal–iron
Advancement in the direct C–H bond alkylation of arenes and heteroarenes using the catalysts based on the most abundant transition metal, iron, is summarized.
Org. Chem. Front., 2024,11, 2397-2417
https://doi.org/10.1039/D4QO00063C
Frustrated Lewis pair chemistry of alkynes
This review is focused on the chemistry of frustrated Lewis pairs (FLPs) with alkynes and surveys the range of stoichiometric and catalytic reactions enabled by this concept.
Org. Chem. Front., 2024,11, 2375-2396
https://doi.org/10.1039/D4QO00217B
Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation
Organofluorine compounds are of high value. NHC-catalyzed fluorination and fluoroalkylation have served as powerful and versatile vehicles for accessing the related organofluorines. This review focuses on the recent developments in this area.
Org. Chem. Front., 2024,11, 2112-2133
https://doi.org/10.1039/D3QO02098C
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
Recent advances in metal-free catalytic enantioselective higher-order cycloadditions
In this review, we briefly summarize the recent research progress in enantioselective higher-order cycloadditions, focusing on the preparation of medium-sized and multicyclic chiral molecules by metal-free catalysis.
Org. Chem. Front., 2024,11, 1824-1842
https://doi.org/10.1039/D4QO00017J
Recent advances in nickel-catalyzed propargylic substitution
This work summarizes recent progress in nickel-catalyzed propargylic substitution reactions, categorizing them based on the diverse types of nucleophiles involved, with a specific focus on exploring asymmetric transformations.
Org. Chem. Front., 2024,11, 1843-1857
https://doi.org/10.1039/D3QO02129G
Recent advances in hydrogen atom transfer induced C(sp3)–H functionalizations initiated by radical addition to alkynes
Recent advances in HAT-induced C(sp3)–H functionalizations triggered by radical addition to alkynes, including 5-exo-trig, 5-endo-trig, 4-exo-trig and 6-endo-trig cyclization cascades, and intermolecular functionalizations, are summarized.
Org. Chem. Front., 2024,11, 1232-1250
https://doi.org/10.1039/D3QO01876H
Advances in photoinduced radical–polar crossover cyclization (RPCC) of bifunctional alkenes
Photoinduced radical–polar crossover cyclization (RPCC) of bifunctional alkenes is of high synthetic utility to produce cyclic products with precise alkene design. This review summarizes the recent representative advances in the field of RPC.
Org. Chem. Front., 2024,11, 895-915
https://doi.org/10.1039/D3QO01929B
Nascent developments in main group element-catalyzed hydrosilylation and dehydrogenative silylation of alkenes and alkynes
Nascent developments in the main group element-catalyzed hydrosilylation of alkenes and alkynes.
Org. Chem. Front., 2024,11, 576-596
https://doi.org/10.1039/D3QO01777J
Enhancing the binding of calix[5]arene containers for ferrocenes by a fluorophobic effect through the release of high-energy perfluoro-1-iodoalkanes
The release of high-energy perfluoro-1-iodohexane molecules has been demonstrated as a major driving force for enhanced binding between calix[5]arene containers and ferrocene guests.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00672K
Aerobic bimetallic catalysis for oxy-alkynylation of allenes
An aerobic double functionalization of 2,3-allenoic acids with terminal alkynes has been achieved affording versatile 4-alkynylfuran-2(5H)-one derivatives, which have been demonstrated as platform molecules for synthesis of useful natural products.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00622D
Four-component regio-divergent carbonylative condensations for the sustainable syntheses of acylhydrazones
Novel catalytic four-component regiodivergent tandem carbonylative condensations of alkenes for the sustainable syntheses of acylhydrazones with high atom economy and excellent chemoselectivity have been developed.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00651H
Bisphosphonium salt catalyzed [3 + 2] annulation of N-tosylimino(iso)quinolinium ylides with aryl olefins under blue LED irradiation
A visible-light-induced [3 + 2] annulation of N-tosylimino(iso)quinolinium ylides with aryl olefins, catalyzed by a bisphosphonium salt has been developed. Furthermore, the synthesis method of the bisphosphonium salts was improved.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00700J
Assembly of ionic supramolecular polymers using a decacationic pillar[5]arene to noncovalently crosslink hyaluronic acid for short DNA delivery
A multicationic pillar[5]arene noncovalently crosslinks hyaluronic acid to afford ionic supramolecular polymers for intramolecular delivery of short DNA.
Org. Chem. Front., 2024,11, 3019-3025
https://doi.org/10.1039/D4QO00447G
Decarbonylative C(sp2)–C(sp2) reductive cross-coupling of aroyl fluorides with aryl bromides by palladium/cobalt co-catalysis
Herein, we report a decarbonylative C(sp2)–C(sp2) reductive cross-coupling of aroyl fluorides with aryl bromides by palladium and cobalt co-catalysis.
Org. Chem. Front., 2024,11, 3012-3018
https://doi.org/10.1039/D4QO00305E
Catalytic oxidative cyclization of α-carbonyl-γ-alkynyl sulfoxonium ylides for stereospecific synthesis of (1Z,3Z)-1,3-bismethyleneisobenzofurans
A new copper(II)-catalyzed reaction of α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfonyl hydrazides in the presence of tert-butyl hydroperoxide (TBHP) is reported, regio- and stereoselectively accessing (1Z,3Z)-1,3-bismethyleneisobenzofurans.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO00735B
Synthesis of a helical boron-doped PAH by post-functionalization of 3,9-diboraperylene
A doubly helical boron-doped polycyclic aromatic hydrocarbon was synthesized, which showed a low LUMO level, a high absorption coefficient and fluorescence (ΦF = 0.73), combined with a one-dimensional π–π stacking interaction in the solid state.
Org. Chem. Front., 2024,11, 2747-2755
https://doi.org/10.1039/D4QO00421C
Synthesis of 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3
Herein we present a practical approach for preparing 10B-enriched 2,1-borazaronaphthalenes from o-aminostyrenes and 10BF3 (the primary source of boron-10) in the presence of chlorosilane.
Org. Chem. Front., 2024,11, 2733-2738
https://doi.org/10.1039/D4QO00176A
Platform for 3-fluoro-3-hydroxyoxindoles: photocatalytic C–N cross-coupling and deaminative oxidation–fluorohydroxylation
A photocatalytic C–N cross-coupling and deaminative fluorinating strategy has been developed to afford 3-fluoro-3-hydroxyoxindoles with wide functionality tolerance and good yields.
Org. Chem. Front., 2024,11, 2727-2732
https://doi.org/10.1039/D4QO00285G
A Mn(III)-catalyzed arylboronic acid-based cascade reaction via a nonclassical organometallic-radical mechanism
An efficient Mn(III)-catalyzed cascade reaction of arylboronic acids, o-cyanoaryl isocyanides, and indoles was developed. The mechanism was fully investigated and elucidated.
Org. Chem. Front., 2024,11, 2739-2746
https://doi.org/10.1039/D4QO00244J
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
Photoinduced copper-catalyzed alkoxycarbonylation of alkyl fluorides
A photoinduced copper-catalyzed alkoxycarbonylation of alkyl fluorides with phenols to synthesize various esters has been developed.
Org. Chem. Front., 2024,11, 2462-2467
https://doi.org/10.1039/D4QO00041B
Palladium-catalyzed siloxycarbonylation of alkenes to synthesize silyl esters
Synthesis of stable acyl intermediates and their transformation for the synthesis of carbonyl derivatives is highly desirable. We have developed a method for the synthesis of stable acyl intermediates, silyl esters, through siloxycarbonylation.
Org. Chem. Front., 2024,11, 2457-2461
https://doi.org/10.1039/D4QO00086B
Stereoselective skeletal modification of tryptanthrins to install chiral piperidine-2-ones enabled by Brønsted acid catalysis
An asymmetric formal [4 + 2] cyclisation between azlactones and aza-dienes derived from simple tryptanthrins has been developed. With this established protocol, yielding a series of novel piperidine-2-one-fused tryptanthrins with up to >99 : 1 er under mild conditions.
Org. Chem. Front., 2024,11, 2171-2177
https://doi.org/10.1039/D3QO02029K
Base-induced azofluoroalkylation of unactivated alkenes via halogen atom transfer
A base-induced three-components coupling employing unactivated alkenes, fluoroalkyl iodides and diazonium salts under mild reaction conditions has been developed.
Org. Chem. Front., 2024,11, 2161-2170
https://doi.org/10.1039/D3QO02114A
Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines
A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via successive regioselective chalcogenation, oxidation, amination and halogenation.
Org. Chem. Front., 2024,11, 1933-1940
https://doi.org/10.1039/D4QO00030G
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
NADH-mediated primordial synthesis of amino acids
Amino acid formation by hydride transfer from NADH without the need for enzymes connects prebiotic chemistry with the metabolic pathways that presumably led to these biomolecules in the first autotrophic protocells.
Org. Chem. Front., 2024,11, 1924-1932
https://doi.org/10.1039/D4QO00050A
Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF3-ynones via C–H/N–H/C–N/C–C bond cleavage
We present a novel synthesis of CF3- and alkynyl-substituted quinoline derivatives based on Rh(III)-catalyzed cascade reactions of N-aryl amidines with two CF3-ynones. Then, some products are transformed into polycyclic CF3-benzo[k]phenanthridines through an intramolecular annulation reaction.
Org. Chem. Front., 2024,11, 1917-1923
https://doi.org/10.1039/D3QO02070C
Dearomative spiroannulation of indoles enabled by the diaza-[1,2]-Wittig rearrangement
Reported herein is the first diaza-[1,2]-Wittig rearrangement-enabled dearomative spiroannulation reaction of indoles. This protocol features metal-free conditions, a redox-neutral process, a broad substrate scope, and a good yield.
Org. Chem. Front., 2024,11, 1685-1691
https://doi.org/10.1039/D3QO02033A
Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis
This method allows for the enantioselective synthesis of β-azide sulfones via iron-catalyzed vicinal azide-sulfonylation of acrylamides. It makes the first instance of achieving asymmetric construction through iron catalysis with SO2 insertion.
Org. Chem. Front., 2024,11, 1678-1684
https://doi.org/10.1039/D3QO02004E
Synthesis of branched-chain sugars and higher-carbon sugars enabled by site-selective C–H alkylation relying on 1,5-hydrogen atom transfer of ethylenoxy radicals
Branched-chain sugars and higher-carbon sugars have been efficiently prepared by site-selective C–H alkylation mediated by 1,5-HAT of ethylenoxy radicals.
Org. Chem. Front., 2024,11, 1332-1340
https://doi.org/10.1039/D3QO02013D
![Open Access](https://www.rsc-cdn.org/pubs-core/2022.0.139/content/NewImages/open-access-icon-orange.png)
Palladium-catalyzed thiocarbonylation of alkenes toward branched thioesters using CO2
Thiocarbonylation of alkenes using CO2 was developed for the preparation of a broad array of thioesters. By the combination of Pd catalyst and N–P type carbazophosphine ligand, the reactivity and selectivity were well tuned.
Org. Chem. Front., 2024,11, 1322-1331
https://doi.org/10.1039/D3QO01940C
Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis
A new class of chiral bipyridine-2NO ligands, which incorporate the advantages of both the bipyridine skeleton and the pyrroloimidazolone-based N-oxide moiety, was developed.
Org. Chem. Front., 2024,11, 1314-1321
https://doi.org/10.1039/D3QO01748F
Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp3)–F activation
A conceptually novel single electron transfer strategy for C(sp3)–F activation-enabled [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes is developed.
Org. Chem. Front., 2024,11, 1305-1313
https://doi.org/10.1039/D3QO02054A
Rapid synthesis of benzofulvenes from α-bromodiarylethylenes based on a 1,4-palladium shift strategy
The synthesis of benzofulvenes from α-halo diarylethylenes through 1,4-palladium migration has been reported. The reaction accepts a variety of functional groups and affords a wide range of functionalized benzofulvenes up to 93% yields.
Org. Chem. Front., 2024,11, 1225-1231
https://doi.org/10.1039/D3QO01846F
Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones
A catalyst-free, photoinduced three-component reaction involving sulfur dioxide insertion/sulfonyl radical addition to an unactivated CC double bond/Minisci-type cyclization sequence has been developed to access sulfonated quinazolinones.
Org. Chem. Front., 2024,11, 1169-1174
https://doi.org/10.1039/D3QO01974H
Obscurinin A, a unique Lycopodium alkaloid possessing an 8/6/6/6/5 pentacyclic system isolated from Lycopodium obscurum L.
Obscurinin A, an unprecedented Lycopodium alkaloid with an 8/6/6/6/5 ring system, showed significant inhibitory activity on the Cav3.1 calcium channel.
Org. Chem. Front., 2024,11, 1163-1168
https://doi.org/10.1039/D3QO01923C
About this collection
Read our on-going collection of the hottest research published as advance article from Organic Chemistry Frontiers in 2024. These articles are recommended by reviewers as being of significant novelty and interest. Congratulations to all the authors whose articles are featured!