Themed collection 2024 Organic Chemistry Frontiers Review-type Articles
Integrating electrocatalysis with biocatalysis for asymmetric synthesis
This highlight presents recent advances in asymmetric synthesis that integrate electrocatalysis with biocatalysis and discusses future development directions in this field.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO01899K
Catalytic asymmetric synthesis of chiral sulfilimines via S-C bond formation
Org. Chem. Front., 2024, Accepted Manuscript
https://doi.org/10.1039/D4QO01963F
Strategic convergent synthesis en route to Veratrum steroidal alkaloids
In this Highlight, the convergent synthetic approaches that yield the highly functionalized, complex molecular architecture of Veratrum steroidal alkaloids are discussed.
Org. Chem. Front., 2024,11, 4014-4023
https://doi.org/10.1039/D4QO00717D
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
Recent advances in the photocatalytic cleavage of C–C and C–N bonds associated with amines and their derivatives
Org. Chem. Front., 2025, Accepted Manuscript
https://doi.org/10.1039/D4QO02038C
Photoinduced Ullmann-Type Cross-Coupling Reactions: Mechanistic Insights and Emerging Challenges
Org. Chem. Front., 2025, Accepted Manuscript
https://doi.org/10.1039/D4QO01814A
Manganese(III) acetate in organic synthesis: a review of the past decade
In this review, we summarize the latest developments and applications of Mn(OAc)3 in organic synthesis over the past decade, focusing on efforts to achieve milder reaction conditions while expanding the scope of synthesis possibilities.
Org. Chem. Front., 2024,11, 6850-6917
https://doi.org/10.1039/D4QO01499E
State-of-the-art strategies for Lewis acid-catalyzed strain-release cycloadditions of bicyclo[1.1.0]butanes (BCBs)
This review primarily focuses on the latest developments in Lewis acid-catalyzed strain-release cycloaddition reactions of BCBs.
Org. Chem. Front., 2024,11, 6942-6957
https://doi.org/10.1039/D4QO01741B
Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions
This review highlights the recent progress in palladium-catalyzed C-glycosylation reactions for the synthesis of C-glycosides.
Org. Chem. Front., 2024,11, 6918-6941
https://doi.org/10.1039/D4QO01619J
Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks
This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications in the development of this class of five-membered heterocyclic frameworks.
Org. Chem. Front., 2024,11, 6819-6849
https://doi.org/10.1039/D4QO01705F
Hydrogen autotransfer with alcohols for alkylations
Iron/ruthenium complexes, akin to Knölker catalysts, for bond reduction and sustainable alkylation using alcohols are included in this review, along with advances in dehydrogenative coupling, hydrogen borrowing, and light-assisted catalysis.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO01626B
Transition-Metal Free Approaches to Access N-Heterocycles and Valuable Intermediates from Aryldiazonium Salts
Org. Chem. Front., 2025, Accepted Manuscript
https://doi.org/10.1039/D4QO01776E
Convergent Synthetic Approaches to Polycyclic Aromatic Dicarboximides
Org. Chem. Front., 2025, Accepted Manuscript
https://doi.org/10.1039/D4QO01828A
Recent advances in carbon atom addition for ring-expanding single-atom skeletal editing
This review focuses on recent advances in carbon atom addition for ring-expanding single-atom skeletal editing.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO01806K
Recent advances in asymmetric synthesis of chiral benzoheterocycles via Earth-abundant metal catalysis
This review mainly focus on the assembly of chiral benzoheterocycles, such as dihydrobenzofurans, chromans, indolines, tetrahydroquinolines, etc., via Earth-abundant metal-catalyzed (Cu, Fe, Ni, and Ti) asymmetric synthesis in the last few decades.
Org. Chem. Front., 2024,11, 6534-6557
https://doi.org/10.1039/D4QO01686F
Shining light on sulfonium salts and sulfur ylides: recent advances in alkylation under photoredox catalysis
Recent advancements in photoredox alkylation with sulfur ylides, sulfonium salts and related analogues are summarized in this review.
Org. Chem. Front., 2024,11, 6573-6588
https://doi.org/10.1039/D4QO01644K
Recent developments in the ring-opening transformations of gem-difluorocyclopropanes
This review summarizes the advances of gem-F2CPs as fluoroallylic synthons in transition metal-catalysed ring-opening/cross-coupling reactions via single, double or no C-F bond cleavage on the last two years.
Org. Chem. Front., 2024,11, 6518-6533
https://doi.org/10.1039/D4QO01583E
Transition-metal-catalyzed C–Ge coupling reactions
This review covers the development and recent progress in transition-metal-catalyzed C–Ge coupling reactions. The goal is to provide a clear overview of the field, identify current challenges, and inspire further applications in this growing area.
Org. Chem. Front., 2024,11, 6558-6572
https://doi.org/10.1039/D4QO01637H
The reactivity of alkenyl boron reagents in catalytic reactions: recent advances and perspectives
Recent advances focusing on novel reactivity of alkenyl boron reagents in polar or radical pathways within catalytic reactions by employing transition metal catalysis, organocatalysis have been summarized and discussed.
Org. Chem. Front., 2024, Advance Article
https://doi.org/10.1039/D4QO01703J
Recent advances in cooperative N-heterocyclic carbenes and photocatalysis
Combination of N-heterocyclic carbene catalysis and photocatalysis with radical process is a powerful strategy to access useful molecules. In this review, we summarized recent advances in this growing area from the perspective of reaction mechanism.
Org. Chem. Front., 2024,11, 6243-6264
https://doi.org/10.1039/D4QO01335B
Transition metal-catalyzed redox-neutral 1,3-dienylation of propargylic esters and divergent synthesis
Stereoselective dienylation of propargylic esters with nucleophiles via transition metal catalysis is a powerful method for accessing conjugated dienes. In particular, divergent synthesis beyond 1,3-dienes can be realized.
Org. Chem. Front., 2024,11, 6231-6242
https://doi.org/10.1039/D4QO01407C
New chemistry of alkynyl trifluoroborates under transition metal catalyst-free conditions
This review summarizes recent advances in alkynyl trifluoroborate chemistry, emphasizing their unique reactivity and stability in organic synthesis and biological applications under transition metal catalyst-free conditions.
Org. Chem. Front., 2024,11, 5985-6003
https://doi.org/10.1039/D4QO01398K
Synthesis and applications of fluorinated, polyfluoroalkyl- and polyfluoroaryl-substituted 1,2,3-triazoles
This review summarises methods to synthesise and apply fluorine- and polyfluoroalkyl/aryl-substituted 1,2,3-triazoles. Focus is devoted to recent examples and those where the properties of both the 1,2,3-triazole and fluorine groups are important.
Org. Chem. Front., 2024,11, 5938-5984
https://doi.org/10.1039/D4QO01334D
Post-functionalization of end-capped twistacenes with pyrene units
This review covers recent advances in post-functionalization of twistacenes to realize polyacenes, chiral nanographenes and their semiconductor properties, and emphasizing a promising future for constructing chiral nanotubes.
Org. Chem. Front., 2024,11, 5638-5669
https://doi.org/10.1039/D4QO01199F
Recent advances in late-stage monofluorination of natural products and their derivatives
In this review, we have discussed the monofluorination of natural products or their derivatives occurring via direct C–H functionalization, late-stage functionalization and late-stage functional group transformation from 2011–2023.
Org. Chem. Front., 2024,11, 5605-5637
https://doi.org/10.1039/D4QO01111B
Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds
This review has summarized the development of organocatalytic asymmetric [3 + 3] cycloadditions and given insights into the remaining challenges to promote the future development of this field.
Org. Chem. Front., 2024,11, 5573-5604
https://doi.org/10.1039/D4QO00515E
Recent advances in electrochemical difunctionalization of alkenes and alkynes for the synthesis of organohalides
This review summarizes recent achievements in electrosynthesis of organohalides through difunctionalization of alkenes and alkynes and provides insights into future directions for the development of the field.
Org. Chem. Front., 2024,11, 5306-5324
https://doi.org/10.1039/D4QO01348D
Modern photo- and electrochemical approaches to aryl radical generation
This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy and resource utilization, thus providing more sustainable radical arylation methods.
Org. Chem. Front., 2024,11, 5232-5277
https://doi.org/10.1039/D4QO00999A
Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects
This review summarizes the latest methodological advances in photocatalytic C(sp3)–H functionalization, with a particular emphasis on the formation of C–P, C–B, C–S bonds, etc., and some prominent efforts in asymmetric C–H functionalization.
Org. Chem. Front., 2024,11, 5278-5305
https://doi.org/10.1039/D4QO01179A
Vinyl radicals in transition metal-catalyzed organic transformations
We summarize the advancements in transition metal-catalyzed organic transformations involving vinyl radicals and provide a categorical overview based on the reaction types.
Org. Chem. Front., 2024,11, 5202-5231
https://doi.org/10.1039/D4QO00995A
Site-selective editing of carbohydrate scaffolds to access rare sugars enabled by photoinduced radical processes
Herein, we summarize recent achievements via photoinduced radical-mediated strategies that enable the precise modification of carbohydrates.
Org. Chem. Front., 2024,11, 4926-4933
https://doi.org/10.1039/D4QO00963K
Recent advancements in Ni/photoredox dual catalysis for Csp3–Csp3 cross-coupling reactions
This minireview highlights recent advancements in the past five years (since 2019) in Ni/photoredox dual catalysis for Csp3–Csp3 cross-coupling reactions.
Org. Chem. Front., 2024,11, 4913-4925
https://doi.org/10.1039/D4QO00887A
Recent advances in post Ugi-4CR dearomatizations for constructing spiro heterocycles
This review summarizes recent advances in the combination of Ugi-4CR and dearomatization for the synthesis of spirocycles.
Org. Chem. Front., 2024,11, 4895-4912
https://doi.org/10.1039/D4QO01060D
Recent progress in asymmetric rearrangement reactions mediated by chiral Brønsted acids
This review presents an overview of recent developments and trends in chiral Brønsted acid mediated rearrangement reactions. Different mechanisms and activation modes are summarized to illustrate the regio- and stereo-selectivity in the reactions.
Org. Chem. Front., 2024,11, 4934-4953
https://doi.org/10.1039/D4QO00807C
Photocatalytic C–P bond formation based on the reaction of carbon-centered radicals with phosphides
This review focuses on the synthesis of C–P bonds using carbon-centered radicals with phosphorous compounds of different valence states (PIII, PV, P4) under photocatalysis.
Org. Chem. Front., 2024,11, 4882-4894
https://doi.org/10.1039/D4QO00933A
Recent advances on carbon nitride-based photocatalysts for organic transformations in aqueous media
This review highlights recent advancements in photocatalytic organic transformations in aqueous media employing the water-compatible solid-state sensitizer carbon nitride and its derivatives as catalysts.
Org. Chem. Front., 2024,11, 4624-4638
https://doi.org/10.1039/D4QO00955J
Catalytic transformations of alkenes via nickelacycles
This review summarizes recent developments in nickel-catalyzed transformations of alkenes via nickelacycles, highlighting the advantages and challenges of this innovative strategy.
Org. Chem. Front., 2024,11, 4602-4623
https://doi.org/10.1039/D4QO00737A
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., 2024,11, 4560-4601
https://doi.org/10.1039/D4QO00535J
Electroreduction strategy: a sustainable tool for the generation of aryl radicals
This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates on synthetic applications, scope, and limitations of the substrates.
Org. Chem. Front., 2024,11, 4318-4342
https://doi.org/10.1039/D4QO00846D
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., 2024,11, 4290-4317
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., 2024,11, 4041-4053
https://doi.org/10.1039/D4QO00812J
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., 2024,11, 4024-4040
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., 2024,11, 3777-3799
https://doi.org/10.1039/D4QO00606B
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., 2024,11, 3729-3776
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
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
Asymmetric gold catalysis enabled by specially designed ligands
This review is planned to provide a comprehensive overview of the progress made in the design and development of chiral ligands for asymmetric gold catalysis.
Org. Chem. Front., 2024,11, 1858-1895
https://doi.org/10.1039/D4QO00057A
Site-selective editing of peptides via backbone modification
The site-selective modifications of peptide backbones have a significant impact on peptide conformation, folding ability, and physicochemical and biological properties. This review discusses the site-selective modifications of peptide backbones and classifies them into four categories.
Org. Chem. Front., 2024,11, 1623-1640
https://doi.org/10.1039/D3QO01980B
Palladium-catalyzed cross-dehydrogenative coupling of (hetero)arenes
A general and authoritative literature overview on Pd-catalyzed cross-dehydrogenative coupling reactions of (hetero)arenes from the origins to 2023, where not only the synthetic aspects were described but also the most relevant mechanistic features.
Org. Chem. Front., 2024,11, 1495-1622
https://doi.org/10.1039/D3QO01925J
Catalyst-free photoarylation reactions promoted by visible light
This review presents significant and selected examples of organic synthesis methods that use visible-light-promoted photoarylation reactions without the need for additional photocatalysts.
Org. Chem. Front., 2024,11, 1251-1275
https://doi.org/10.1039/D3QO01738A
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
Enantioselective synthesis of chiral BCPs
This article reviews the methodologies available for the asymmetric synthesis of chiral BCPs via enantioselective transformations of BCPs or direct asymmetric functionalization of [1.1.1]propellane.
Org. Chem. Front., 2024,11, 916-928
https://doi.org/10.1039/D3QO01631E
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
C–H borylation: a tool for molecular diversification
Iridium-catalyzed C–H activation and borylation has become as a powerful synthetic tool in the past few decades because of the widespread applicability and versatility of organoboron compounds.
Org. Chem. Front., 2024,11, 929-953
https://doi.org/10.1039/D3QO01931D
Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation
The review summarises various photo- and electrochemical strategies for trifluoromethylation and fluoroalkylation of different C(sp3)–H, C(sp2)–H, and C(sp)–H bonds in several classes of organic molecules.
Org. Chem. Front., 2024,11, 954-1014
https://doi.org/10.1039/D3QO01603J
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
About this collection
Critical reviews, highlights and chemistry frontiers articles published in Organic Chemistry Frontiers during 2024 are collated as below for the benefit of readers.