Themed collection 2023 Organic Chemistry Frontiers Review-type Articles
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Ligand relay catalysis: a newly emerged synthetic strategy
Ligand relay catalysis, which brings a new way to broaden the SMMLC strategy, has recently been developed and discussed. This strategy acts as a powerful way, broadening the range of catalytic transformations to construct highly functional molecules.
Org. Chem. Front., 2023,10, 4146-4160
https://doi.org/10.1039/D3QO00913K
Feng chiral N,N′-dioxide ligands: uniqueness and impacts
Privileged Feng ligands feature designer N,N’-dioxide amides with a unique conformational and coordination flexibility. This highlight summarizes the increasingly profound impact of Feng ligands on modern catalytic asymmetric synthesis.
Org. Chem. Front., 2023,10, 3676-3683
https://doi.org/10.1039/D3QO00566F
Methylene-bridged naphthotubes: new macrocyclic arenes with great potential for supramolecular chemistry
This highlight discusses a recent study reported by Quan, Jiang and co-workers where a new class of macrocyclic arenes with well-defined cavities, namely methylene-bridged naphthotubes, were prepared.
Org. Chem. Front., 2023,10, 2340-2345
https://doi.org/10.1039/D3QO00258F
Transformations based on direct excitation of hypervalent iodine(III) reagents
Hypervalent iodine compounds became an important class of reagents in synthesis. In this review, we present reactivity patterns of five different structural classes of hypervalent iodine compounds and their complexes under visible light irradiation.
Org. Chem. Front., 2023,10, 1577-1586
https://doi.org/10.1039/D3QO00039G
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Shape-shifting p-cyclophanes as portals to switching, sensing, delivery and logic operations in water
Switchable cyclophanes allow capture/release of guests to control their properties.
Org. Chem. Front., 2023,10, 1570-1576
https://doi.org/10.1039/D2QO02043B
Emerging applications of acylsilanes in organic synthesis and beyond
The last two years have witnessed unprecedentedly wide applications of acylsilanes in many fields well beyond pure organic synthesis. This highlight covers selected representative examples and focuses on their possible applications in the future.
Org. Chem. Front., 2023,10, 1316-1321
https://doi.org/10.1039/D2QO02010F
Directing group-assisted selective C–H activation of six-membered N-heterocycles and benzo-fused N-heterocycles
Directing group-assisted selective C–H bond activation of six-membered N-heterocycles and benzo-fused N-heterocycles has been reported.
Org. Chem. Front., 2024,11, 540-575
https://doi.org/10.1039/D3QO01396K
A route to carbon-sp3 bridging spiro-molecules: synthetic methods and optoelectronic applications
Molecules with spiro-linked π-conjugated structures have attracted considerable attention in the realm of organic functional materials due to their advantageous structural features.
Org. Chem. Front., 2024,11, 508-539
https://doi.org/10.1039/D3QO01735D
Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation
This review highlights the recent progress in the electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.
Org. Chem. Front., 2024,11, 597-630
https://doi.org/10.1039/D3QO01844J
Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions
In this review, we elaborate and discuss the recent applications of straight-chain amino-α,β-unsaturated carbonyl compounds as versatile synthons in organocatalytic reactions for the creation of five- and six-membered saturated nitrogen-containing heterocycles.
Org. Chem. Front., 2024,11, 236-253
https://doi.org/10.1039/D3QO01734F
Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides
This review summarizes the latest achievements in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides and focuses on the novel features and proposed mechanisms.
Org. Chem. Front., 2024,11, 217-235
https://doi.org/10.1039/D3QO01610B
Tetraphenylethene-based macrocycles with dual-ring topology: synthesis, structures, and applications
This review focuses on the eight-shaped double ring structure of tetraphenylethylene, summarizes the research progress of structures, ionic molecular structures and metal molecular structures, and looks forward to its future development direction.
Org. Chem. Front., 2023,10, 6225-6239
https://doi.org/10.1039/D3QO01426F
BX3-mediated borylation for the synthesis of organoboron compounds
This review summarizes the recent progress in borylation driven by BX3 in the fields of organic synthesis and drug synthesis.
Org. Chem. Front., 2023,10, 6010-6020
https://doi.org/10.1039/D3QO01487H
Nucleophilic organocatalysis involving radical intermediates
The recent advancements in single-electron nucleophilic organocatalysis that facilitates single-electron transfer between substrates through the formation of a covalent intermediate were summarized based on the type of catalyst.
Org. Chem. Front., 2023,10, 6021-6040
https://doi.org/10.1039/D3QO01435E
Recent advances in trifluoroethylation reaction
The recent advances in trifluoroethylation reactions were summarized based on the bond formation: C(sp)–CH2CF3, C(sp2)–CH2CF3, C(sp3)–CH2CF3, and X (X = N, O, S, Se)–CH2CF3.
Org. Chem. Front., 2023,10, 5986-6009
https://doi.org/10.1039/D3QO01366A
C–F bond functionalizations via fluorinated carbenes
This feature article summarizes the developments in fluorinated carbene transformations, and their consequent C–F functionalization in a cascade platform.
Org. Chem. Front., 2023,10, 5782-5804
https://doi.org/10.1039/D3QO01461D
Recent progress on radiofluorination using metals: strategies for generation of C–18F bonds
This review summarizes recent progress in metal-mediated radiofluorination studies for C–18F bond formation to provide organofluorine-18 compounds.
Org. Chem. Front., 2023,10, 5746-5781
https://doi.org/10.1039/D3QO00772C
Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization
Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide a summary of the advancements achieved in metal-catalyzed C–H functionalization using VC.
Org. Chem. Front., 2023,10, 5717-5734
https://doi.org/10.1039/D3QO01227A
Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions
During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for the efficient formation of chemical bonds.
Org. Chem. Front., 2023,10, 5735-5745
https://doi.org/10.1039/D3QO01482G
β-Trifluoromethylated enones as trifluoromethylated synthons in asymmetric catalysis
This minireview describes the applications of β-trifluoromethylated enones in diverse asymmetric catalytic transformations since 2008, and incorporates the mechanistic aspects, involving the key mechanistic intermediates and the reaction pathways.
Org. Chem. Front., 2023,10, 5519-5537
https://doi.org/10.1039/D3QO01357J
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Celastraceae sesquiterpene pyridyl ligands
Celastraceae sesquiterpene alkaloids display an array of biological properties and comprise oxygenated dihydroagarofuran cores often adorned with pyridyl macrodilactone bridging ligands. Here, the history and syntheses of these ligands are reviewed.
Org. Chem. Front., 2023,10, 5296-5308
https://doi.org/10.1039/D3QO01011B
Recent advances in electrochemical C–H bond amination
.This review summarizes recent developments in electrochemical C–H amination, highlighting key inspirations and proposed mechanisms behind these sustainable oxidation-free approaches for constructing C–N bonds directly from C–H bonds.
Org. Chem. Front., 2023,10, 5309-5330
https://doi.org/10.1039/D3QO01159C
Strained cycloalkanols in C–C bond formation reactions: a boon in disguise!
A summary of the various ring opening reactions of strained and unstrained cycloalkanols is elaborated in the present review. Key emphasis on the reactivities pertaining to cyclopropanols, cyclobutanols and higher unstrained analogues is provided.
Org. Chem. Front., 2023,10, 4941-4971
https://doi.org/10.1039/D3QO01090B
Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds
This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on the mechanistic insights of these transformations.
Org. Chem. Front., 2023,10, 4488-4515
https://doi.org/10.1039/D3QO01010D
Lighting the way to diverse cyclic architectures: expanding the horizons with photogenerated ketenes in sustainable chemistry
Photogenerated ketenes simplify and accelerate the synthesis of diverse cyclic architectures and demonstrate their promising applications in flow chemistry.
Org. Chem. Front., 2023,10, 4474-4487
https://doi.org/10.1039/D3QO00831B
Catalyst-controlled stereoselective carbon–heteroatom bond formations by N-heterocyclic carbene (NHC) organocatalysis
This review highlights recent advances in stereoselective carbon–heteroatom bond forming reactions, including C–N, C–O, C–S, C–F, C–P, etc., that were enabled by NHC organocatalysis with a focus on new activation modes and reactive intermediates.
Org. Chem. Front., 2023,10, 4437-4458
https://doi.org/10.1039/D3QO00667K
Recent advances in the application of ligands in palladium-catalyzed chemoselective coupling reactions at C–Br, C–OTf, and C–Cl sites
This article presents a comprehensive analysis of the progress in palladium-catalyzed coupling reactions, with an emphasis on how ligand characteristics affect the chemoselectivity of aryl (pseudo)halides.
Org. Chem. Front., 2023,10, 4408-4436
https://doi.org/10.1039/D3QO00640A
Recent advances in the photocatalytic synthesis of aldehydes
This review summarizes the recently developed photocatalytic strategies for the installation of the formyl group into various scaffolds.
Org. Chem. Front., 2023,10, 4198-4210
https://doi.org/10.1039/D3QO01026K
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New advances in chiral nanographene chemistry
This review will highlight several recent and lesser-reviewed works related to the preparation of chiral nanographenes, specifically focusing on structures prepared by non-Scholl methods.
Org. Chem. Front., 2023,10, 4167-4197
https://doi.org/10.1039/D3QO00517H
Recent advances in electrochemical synthesis of diversely functionalized oxindole derivatives
This review will focus on the electrochemical synthesis of diversified functionalized oxindole derivatives through C-S, C-O, C-C, C-Se, and C-N bond formation over the past decade.
Org. Chem. Front., 2023,10, 3929-3950
https://doi.org/10.1039/D3QO00671A
Transition-metal-catalyzed asymmetric defluorinative reactions
The latest achievements in transition-metal-catalyzed enantioselective defluorinative coupling reactions have been comprehensively summarized on the basis of the classification of transition-metal catalysts.
Org. Chem. Front., 2023,10, 3909-3928
https://doi.org/10.1039/D3QO00751K
Recent advances in the chemistry of α-oxylboronate reagents
The synthesis and transformation of α-oxylboronates including their C–B bond and C–O bond functionalizations are reviewed.
Org. Chem. Front., 2023,10, 3684-3700
https://doi.org/10.1039/D3QO00521F
Recent progress on the chemical synthesis of bacterial non-2-ulosonic acids
A summary of the chemical syntheses of bacterial non-2-ulosonic acids and their derivatives via de novo synthetic approaches starting from non-sugar compounds and total synthesis starting from sugar material.
Org. Chem. Front., 2023,10, 3429-3446
https://doi.org/10.1039/D3QO00637A
Recent advances in intramolecular kinetic resolution reactions
This review summarizes the advances in the field of intramolecular kinetic resolution (KR) mediated by non-enzymatic catalysts. The relative classification of intramolecular KR is accomplished and several categories of reactions are discussed.
Org. Chem. Front., 2023,10, 3401-3428
https://doi.org/10.1039/D3QO00563A
Applications of trisulfide radical anion S3˙− in organic synthesis
The synthetic and mechanistic aspects of the role of the trisulfide radical anion S3˙− in organic chemistry are reviewed.
Org. Chem. Front., 2023,10, 3378-3400
https://doi.org/10.1039/D3QO00496A
Electrochemical synthesis and transformation of organoboron compounds
This review highlights the recent advances in both electrochemical borylation and hydroboration to synthesize organoboron compounds and electrochemical transformation of organoboron compounds to construct carbon–carbon and carbon–heteroatom bonds.
Org. Chem. Front., 2023,10, 3361-3377
https://doi.org/10.1039/D3QO00486D
Recent advances in the asymmetric catalytic construction of oxa-quaternary carbon centers
This review focuses on the very recent advances (from 2020 to the beginning of 2023) in enantioselective catalytic reactions for the construction of oxa-quaternary stereocenters.
Org. Chem. Front., 2023,10, 3110-3129
https://doi.org/10.1039/D3QO00527E
Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species
This review summarizes a view of the advances in the catalytic asymmetric α-functionalization of vinylogous nucleophilic species, the content of which is categorized based on the type of vinylogous donor.
Org. Chem. Front., 2023,10, 3130-3168
https://doi.org/10.1039/D3QO00506B
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Chiral organophosphates as ligands in asymmetric metal catalysis
Chiral phosphates have successfully been used as ligands in asymmetric metal-catalysis. This Minireview discusses the most recent examples, including main-group catalysis, transition-metal catalysis and catalysis by rare-earth metals.
Org. Chem. Front., 2023,10, 3080-3109
https://doi.org/10.1039/D3QO00206C
Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds
Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights and synthetic applications have been summarized.
Org. Chem. Front., 2023,10, 2830-2848
https://doi.org/10.1039/D3QO00408B
Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism
This review summarizes the recent advances in cyclization reactions involving pyridinium 1,n-zwitterions (n = 4 and 5) and highlights the applications of pyridinium 1,n-zwitterions (n = 4 and 5) in the efficient construction of heterocycles.
Org. Chem. Front., 2023,10, 2813-2829
https://doi.org/10.1039/D3QO00228D
Dirhodium: carbene transformations and beyond
Dirhodium-catalyzed transformations, not limited to carbene and nitrene transfer reactions, are reviewed, including cycloisomerization, hetero-Diels–Alder (HDA) reactions, ene reactions, arylation, radical oxidation reactions and C–H activation, etc.
Org. Chem. Front., 2023,10, 2849-2878
https://doi.org/10.1039/D3QO00400G
Functional supramolecular aggregates based on BODIPY and aza-BODIPY dyes: control over the pathway complexity
The recent advances in the supramolecular assembly of BODIPY and aza-BODIPY dyes are reviewed, emphasizing the control over the kinetic pathway complexity of this class of dyes, and the prospects for future research are summarized.
Org. Chem. Front., 2023,10, 2581-2602
https://doi.org/10.1039/D3QO00148B
N-Amino pyridinium salts in organic synthesis
This review summarizes the synthesis and reactivity of N-aminopyridinium salts, discusses applications in organic synthesis, and highlights the potential for these reagents to enable novel synthetic disconnections and innovations.
Org. Chem. Front., 2023,10, 2563-2580
https://doi.org/10.1039/D3QO00190C
Gold-catalyzed multicomponent reactions
Multicomponent reactions (MCRs) have emerged as an important branch in organic synthesis for the creation of complex molecular structures. This review is focused on gold-catalyzed MCRs with a special emphasis on the recent developments.
Org. Chem. Front., 2023,10, 2359-2384
https://doi.org/10.1039/D3QO00272A
Cyclopropylcarbinyl cation chemistry in synthetic method development and natural product synthesis: cyclopropane formation and skeletal rearrangement
In this Review, the underrecognized utilities of the cyclopropylcarbinyl cation chemistry are summarized in cyclopropane synthesis and skeletal rearrangements, and their applications in natural product total synthesis are highlighted.
Org. Chem. Front., 2023,10, 2346-2358
https://doi.org/10.1039/D3QO00282A
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Selective preparative ‘oxidase phase’ in sesquiterpenoids: the radical approach
Juggling between reactivity and selectivity, free radical oxidation offers a unique means to synthesize natural products in a direct and efficient way. The case study of sesquiterpenes is illustrative of how modern total synthesis should be conducted.
Org. Chem. Front., 2023,10, 2095-2114
https://doi.org/10.1039/D3QO00314K
Transition metal-catalyzed alkynylation reactions via alkynyl carbon–carbon bond cleavage
This review focuses on the representative examples and most recent progresses in transition-metal-catalyzed cleavage of carbon–alkyne bonds in alkynoic acids, propargylic alcohols, alkynyl esters, and alkynyl ketones.
Org. Chem. Front., 2023,10, 2081-2094
https://doi.org/10.1039/D3QO00225J
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Recent advances in aza Friedel–Crafts reaction: strategies for achiral and stereoselective synthesis
The aza-Friedel–Crafts (aza-FC) reaction is a very powerful tool for forming C–C and C–N bonds, based on an acid-catalyzed addition of electron-rich aromatic compounds to imines.
Org. Chem. Front., 2023,10, 1847-1866
https://doi.org/10.1039/D2QO02018A
Active ester-based peptide bond formation and its application in peptide synthesis
Active ester method is an efficient strategy to address the notorious racemization/epimerization issue of peptide bond formation. Herein, the pros and cons of using active esters for peptide synthesis were systematically summarized and analyzed.
Org. Chem. Front., 2023,10, 1817-1846
https://doi.org/10.1039/D2QO01686A
Recent developments on 1,2-difunctionalization and hydrofunctionalization of unactivated alkenes and alkynes involving C–S bond formation
Functionalization of alkenes/alkynes is a highly effective route to achieve molecular complexity. This review summarizes recent progresses on the 1,2-difunctionalization/hydrofunctionalization of unactivated alkenes/alkynes with C−S bond formation.
Org. Chem. Front., 2023,10, 1322-1345
https://doi.org/10.1039/D2QO01699K
10th anniversary of discovering cGAMP: synthesis and beyond
This article describes how the synergy between chemistry and biology facilitated the development of cyclic dinucleotides as a potential new treatment for cancer.
Org. Chem. Front., 2023,10, 1086-1098
https://doi.org/10.1039/D2QO02033E
Radical acylation: concepts, synthetic applications and directions
In this tutorial, reaction scopes, limitations and mechanisms of radical acylations are summarized and discussed according to reaction types and catalytic systems.
Org. Chem. Front., 2023,10, 1056-1085
https://doi.org/10.1039/D2QO01846B
Recent progress and perspectives in photo-induced organic reactions of acylsilanes
This review provides recent advances and insights into photoirradiation reactions of acylsilanes, notably via key nucleophilic siloxycarbene intermediates. Nucleophilic addition, insertion reaction, and cyclization are discussed in terms of reaction mechanism and scope.
Org. Chem. Front., 2023,10, 819-836
https://doi.org/10.1039/D2QO01772E
Exploiting the reactivities of ortho-alkynyl aryl ketones: opportunities in designing catalytic annulation reactions
We provide a comprehensive overview of recent progress in this rapidly growing field by summarizing catalytic annulation reactions of ortho-alkynyl aryl ketones which involve carbo- and oxo-cyclization patterns with consideration of their mechanisms and applications.
Org. Chem. Front., 2023,10, 570-589
https://doi.org/10.1039/D2QO01805E
Exploring visible light for carbon–nitrogen and carbon–oxygen bond formation via nickel catalysis
In this review, we highlight the recent synthetic methodology development for the formation of C–N and C–O bonds via visible-light-driven nickel catalysis, with in-depth discussions with reaction designs and mechanistic scenarios.
Org. Chem. Front., 2023,10, 548-569
https://doi.org/10.1039/D2QO01700H
Eosin Y mediated photo-catalytic C–H functionalization: C–C and C–S bond formation
C–C and C–S bonds are valuable in organic transformation for synthesizing various bioactive heterocycles.
Org. Chem. Front., 2023,10, 237-266
https://doi.org/10.1039/D2QO01534J
Visible light metallaphotoredox catalysis in the late-stage functionalization of pharmaceutically potent compounds
The late stage functionalization (LSF) is a distinctive approach for accelerating the discovery of structure–activity relationships (SARs) and optimising ADME (absorption, distribution, metabolism, and excretion) profiles.
Org. Chem. Front., 2023,10, 216-236
https://doi.org/10.1039/D2QO01582J
Recent development of allyl–allyl cross-coupling and its application in natural product synthesis
This review summarises the significant advancements of allyl–allyl cross-coupling reaction that have provided access to a wide variety of 1,5 dienes and its application in natural product synthesis.
Org. Chem. Front., 2023,10, 267-281
https://doi.org/10.1039/D2QO01078J
Direct coupling of inert C–H bonds in NHC organocatalysis
Direct coupling of inert C–H bonds by NHCs offers efficient routes for the synthesis of functional molecules. Consequently, this highlight presents the latest advancements in NHC-catalyzed latent C–H functionalization involving the ET/PT pathways and HAT pathway.
Org. Chem. Front., 2023,10, 5291-5295
https://doi.org/10.1039/D3QO01129A
The B
C bond: some recent developments
The facile deprotonation of fluoroaryl-substituted alkylboranes or alkylboron cations readily leads to anionic boratalkenes or neutral boraalkenes, respectively. These BC double bond systems exhibit an increasing variety of chemical reactivities.
Org. Chem. Front., 2023,10, 4161-4166
https://doi.org/10.1039/D3QO00796K
A strategy for regioselective B–H functionalization of o-carboranes via base metal catalysis
This frontier article summarizes the recent developments in base metal-catalyzed regioselective cage B–H functionalization of carboranes and discusses the related challenging issues.
Org. Chem. Front., 2023,10, 3074-3079
https://doi.org/10.1039/D3QO00621B
Precise synthesis of schwarzite carbon: hypothesis or reality?
This study summarizes the research progress of schwarzite carbon and presents the theoretical prediction of key units in Schwarzite P192.
Org. Chem. Front., 2023,10, 2808-2812
https://doi.org/10.1039/D3QO00202K
Abundant metal-catalyzed carbonylation of alkyl bromides and alkyl chlorides
Our recent studies on abundant metal (Fe, Cu, and Mn) catalyzed carbonylative transformation of alkyl bromides and alkyl chlorides have been discussed here.
Org. Chem. Front., 2023,10, 1587-1591
https://doi.org/10.1039/D3QO00158J
About this collection
Critical reviews, highlights and chemistry frontiers articles published in Organic Chemistry Frontiers during 2023 are collated as below for the benefit of readers.