Themed collection 2022 Organic Chemistry Frontiers Review-type Articles
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Organogermanium(IV) compounds in photo-induced radical reactions
Behaviors of typical organogermanium(IV) compounds in photo-induced reactions are reviewed.
Org. Chem. Front., 2022,9, 7016-7027
https://doi.org/10.1039/D2QO01467J
Recent progress in the application of iodonium ylides in organic synthesis
This review summarizes the recent advances in the synthetic application of iodonium ylides covering 2017 to 2022.
Org. Chem. Front., 2022,9, 6999-7015
https://doi.org/10.1039/D2QO01332K
Recent advances in the total synthesis of cytochalasan natural products using bioinspired strategies
This review summarizes the recent advances in the bioinspired synthesis of cytochalasans, pentacyclic cytochalasans and merocytochalasans covering from 2016 to 2021.
Org. Chem. Front., 2022,9, 6979-6998
https://doi.org/10.1039/D2QO01223E
Recent developments in enantioselective nickel(II)-catalyzed conjugate additions
This review updates the field of enantioselective nickel-catalyzed conjugate additions since 2016.
Org. Chem. Front., 2022,9, 6717-6748
https://doi.org/10.1039/D2QO01047J
Recent advances in Cu-catalyzed carbonylation with CO
Transition metal-catalyzed carbonylation has emerged as a powerful and versatile strategy for the efficient construction of complicated carbonyl-containing molecules from simple chemical feedstocks in the past decades.
Org. Chem. Front., 2022,9, 6749-6765
https://doi.org/10.1039/D2QO01419J
Recent advances in thiolation via sulfur electrophiles
This review systematically summarizes the recent developments for constructing sulfur compounds from sulfur electrophiles, and the mechanism mainly involved thirranium ions, sulfur ylides, C–S cross coupling and electrophilic substitution.
Org. Chem. Front., 2022,9, 6684-6707
https://doi.org/10.1039/D2QO01447E
Five-membered carbocycle construction in the synthesis of Daphniphyllum alkaloids: recent strategic and methodological advances
In this review article, we summarize novel or non-standard strategies and methods for the five-membered carbocycle construction in recent Daphniphyllum alkaloid synthesis.
Org. Chem. Front., 2022,9, 6708-6716
https://doi.org/10.1039/D2QO01410F
Functionalized 1,3,5-triazine derivatives as components for photo- and electroluminescent materials
Synthetic approaches for 2,4,6-trisubstituted-1,3,5-triazine systems are analyzed, and their properties attractive to practical applications in fluorescent materials are reviewed.
Org. Chem. Front., 2022,9, 6646-6683
https://doi.org/10.1039/D2QO00961G
Recent developments in calix[4]pyrrole (C4P)-based supramolecular functional systems
Recent advances with calix[4]pyrrole-based supramolecular functional entities in the fields of molecular recognition (receptors, sensors, and metal ion caged systems), self-assembly (polymers), photo/pH-responsive molecular switches and catalysis are reviewed.
Org. Chem. Front., 2022,9, 6416-6440
https://doi.org/10.1039/D2QO01298G
Recent advances in photo- and electro-enabled radical silylation
This review aims to highlight the recent advances in the area of radical type silylation reactions mediated by photo- and electrocatalysis.
Org. Chem. Front., 2022,9, 6400-6415
https://doi.org/10.1039/D2QO01387H
Advances in circularly polarized electroluminescence based on chiral TADF-active materials
This review summarizes the development status of chiral TADF-active materials with CPEL, covering chiral perturbed TADF molecules, intrinsically chiral TADF molecules, and TADFsensitized fluorescent enantiomers.
Org. Chem. Front., 2022,9, 6441-6452
https://doi.org/10.1039/D2QO01383E
An overview of the applications of chiral phosphoric acid organocatalysts in enantioselective additions to C
O and C
N bonds
Since 2004, chiral phosphoric acids (CPAs) have emerged as highyl efficient organocatalysts, providing excellent results in a wide reaction scope. In this review, the applications of CPA for enantioselective additions to CO and CN bonds are covered.
Org. Chem. Front., 2022,9, 6331-6399
https://doi.org/10.1039/D2QO01209J
Radical coupling reactions of hydrazines via photochemical and electrochemical strategies
Hydrazines are versatile building blocks in organic synthesis.
Org. Chem. Front., 2022,9, 6114-6128
https://doi.org/10.1039/D2QO01348G
Exploring the synthetic application of sulfinyl radicals
This review summarized the applications of sulfinyl radicals in organic chemistry and thoroughly examined the challenges and future development trends of sulfinyl radicals in modern organic chemistry, as well as their structures and properties.
Org. Chem. Front., 2022,9, 6063-6076
https://doi.org/10.1039/D2QO01403C
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Catalysts’ evolution in the asymmetric conjugate addition of nitroalkanes to electron-poor alkenes
This review provides a journey of the catalyst usage for the enantioselective conjugate addition of nitroalkanes to electron-poor olefins from the early attempts to the latest achievements. Selected applications are also reported.
Org. Chem. Front., 2022,9, 6077-6113
https://doi.org/10.1039/D2QO01341J
Thermodynamics of the elementary steps of organic hydride chemistry determined in acetonitrile and their applications
This review focuses on the thermodynamics of the elementary step of 421 organic hydrides and unsaturated compounds releasing or accepting hydride or hydrogen determined in acetonitrile as well as their potential applications.
Org. Chem. Front., 2022,9, 6001-6062
https://doi.org/10.1039/D2QO01310J
Recent advances in zig-zag-fused BODIPYs
Recent progress in the synthesis of zig-zag-fused BODIPY, structure–property relationships, as well as their applications are summarized.
Org. Chem. Front., 2022,9, 5989-6000
https://doi.org/10.1039/D2QO01243J
Recent advances in the cascade reactions of enynols/diynols for the synthesis of carbo- and heterocycles
This review summaries a view of the advances in the cascade reactions of enynols/diynols for the construction of carbo- and heterocycles.
Org. Chem. Front., 2022,9, 5643-5674
https://doi.org/10.1039/D2QO01154A
C-centered radical-initiated cyclization by directed C(sp3)–H oxidative functionalization
C(sp3)–H functionalization is attracting constant attention. This review emphasizes C-centered radicals initiated cyclization strategies by directed C(sp3)–H oxidative functionalization since 2012.
Org. Chem. Front., 2022,9, 5726-5757
https://doi.org/10.1039/D2QO01128J
Dioxiranes: a half-century journey
Dioxiranes are extremely useful multitasking agents for a broad spectrum of chemical transformations. This review collates the history of dioxiranes over the last fifty years in the realm of organic and materials chemistry.
Org. Chem. Front., 2022,9, 5675-5725
https://doi.org/10.1039/D2QO01005D
Towards better syntheses of partially methylated carbohydrates?
We give an overview of the reported synthetic strategies towards partially methylated glycosides and discuss how better protocols could stem from catalytic site-selective transformations of carbohydrates and cleaner methylation reagents.
Org. Chem. Front., 2022,9, 5414-5425
https://doi.org/10.1039/D2QO00893A
Natural product total synthesis using rearrangement reactions
The synthetic utility of rearrangement reactions in total synthesis for the rapid construction of core skeletons, the precise control of stereochemistry, and the identification of suitable synthons has been discussed.
Org. Chem. Front., 2022,9, 5383-5394
https://doi.org/10.1039/D2QO01040B
Recent advances in catalytic oxidative reactions of phenols and naphthalenols
This critical review aims to provide an overview of oxidative phenol and naphthalenol transformations in nature and synthetic chemistry.
Org. Chem. Front., 2022,9, 5395-5413
https://doi.org/10.1039/D2QO00758D
Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review
In this review, the advances made over the last 6 years in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium and ammonium ylides, as well as diazo compounds and carbenes are summarized.
Org. Chem. Front., 2022,9, 5358-5382
https://doi.org/10.1039/D2QO00698G
Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones
The review highlights the transition metal-free methodologies developed for synthesising various heterocyclic compounds by utilising α,β-unsaturated ketones as valuable synthons during the period of 2009 to 2020.
Org. Chem. Front., 2022,9, 5306-5357
https://doi.org/10.1039/D2QO00278G
Merging dearomatization with redox-neutral C(sp3)–H functionalization via hydride transfer/cyclization: recent advances and perspectives
This review highlights the encouraging advances in hydride transfer-involved dearomatization reaction during the past decade, the content of which is categorized according to the hydride acceptors, namely vinylogous imines and quinone methides.
Org. Chem. Front., 2022,9, 5041-5052
https://doi.org/10.1039/D2QO01054B
Recent advances in the metal-catalyzed asymmetric synthesis of chiral allenes
Recent advances in the metal-catalyzed asymmetric synthesis of chiral allenes are summarized. This review is categorized based on the starting material, including alkynes, racemic allenes, and conjugated dienes.
Org. Chem. Front., 2022,9, 5053-5073
https://doi.org/10.1039/D2QO00994C
Nickel-catalyzed hydroarylation reaction: a useful tool in organic synthesis
The nickel-catalyzed hydroarylation reaction opens up new routes to access complex organic compounds in a highly regio and stereoselective fashion from easily available precursors, such as olefin, alkyne, arene, aryl halide, and aryl boronic acid.
Org. Chem. Front., 2022,9, 5074-5103
https://doi.org/10.1039/D2QO00826B
Recent developments on NHC-driven dual catalytic approaches
This article takes an in depth look at the early relay combination of NHC and other catalysts, and the latest progress in dual catalysis, analyzing the breakthroughs and limitations.
Org. Chem. Front., 2022,9, 5016-5040
https://doi.org/10.1039/D2QO00721E
Recent advances in catalytic asymmetric [1,3]-rearrangement reactions
This review covering the recent advances of asymmetric 1,3-rearrangement reactions is divided into four different fields, including transition metal catalysis, nucleophilic catalysis, Brønsted acid catalysis and Lewis acid catalysis.
Org. Chem. Front., 2022,9, 4744-4756
https://doi.org/10.1039/D2QO01027E
Multiple [n]helicenes with various aromatic cores
Usually, multiple [n]helicene molecules have a characteristic aromatic core, such as benzene, naphthalene, pyrene, perylene, hexabenzocoronene, corannulene, or azacorannulene.
Org. Chem. Front., 2022,9, 4726-4743
https://doi.org/10.1039/D2QO00988A
The synthesis of seven- and eight-membered rings by radical strategies
Radical strategies for preparation of seven- or eight-membered rings.
Org. Chem. Front., 2022,9, 4757-4781
https://doi.org/10.1039/D2QO00774F
Catalytically atroposelective ring-opening of configurationally labile compounds to access axially chiral biaryls
In this minireview, we evaluate and summarize the construction of axially chiral biaryls, and briefly state our personal perspectives on the future advancement of this direction.
Org. Chem. Front., 2022,9, 4507-4521
https://doi.org/10.1039/D2QO00946C
Radical addition to the C
C bond meets (1,n)-HAT: recent advances in the remote C(sp3)–H or C(sp2)–H functionalization of alkenes
This review summarizes the recent development of remote C(sp3)–H bond or aldehydic C(sp2)–H functionalizations enabled by intermolecular radical addition to CC bond/(1,n)-HAT tandem sequences.
Org. Chem. Front., 2022,9, 4490-4506
https://doi.org/10.1039/D2QO00793B
Recent advances in the transformations of different types of Stemona alkaloids
Transformations among Stemona alkaloids with different ring systems have improved the synthetic efficiency toward diverse alkaloids. Recent advances in the transformations of different types of Stemona alkaloids were reviewed for the first time.
Org. Chem. Front., 2022,9, 4478-4489
https://doi.org/10.1039/D2QO00789D
Difluoromethylation of heterocycles via a radical process
In this review, we summarize the state-of-the-art advances in difluoromethylation of heterocycles via a radical process over the past few years (2018 to early 2022).
Org. Chem. Front., 2022,9, 4192-4208
https://doi.org/10.1039/D2QO00762B
Covalent organic frameworks and multicomponent reactions: an endearing give-and-take relationship
MCRs as privileged and practical synthetic route, have been deployed for preparation of COFs. Subsequently, proficient COFs as robust catalysts have been employed for the sustainable MCRs.
Org. Chem. Front., 2022,9, 4178-4191
https://doi.org/10.1039/D2QO00697A
Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry
This review summarizes recent advances in the use of isocyanide as “C1N1” synthons in cyclization.
Org. Chem. Front., 2022,9, 4209-4220
https://doi.org/10.1039/D2QO00753C
Application of a transient directing strategy in cyclization reactions via C–H activation
This review introduces seven types of cyclization reactions via C–H activation using a transient directing strategy.
Org. Chem. Front., 2022,9, 3882-3896
https://doi.org/10.1039/D2QO00765G
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Iodonitrene: a direct metal-free electrophilic aminating reagent
Iodonitrene is a new type of reactive electrophilic aminating reagent that opens up opportunities for new discoveries.
Org. Chem. Front., 2022,9, 3897-3907
https://doi.org/10.1039/D2QO00739H
Partial reductions of carboxylic acids and their derivatives to aldehydes
Recent advances in partial reductions of inert carboxylic acids and their derivatives to active aldehydes are reviewed.
Org. Chem. Front., 2022,9, 3908-3931
https://doi.org/10.1039/D2QO00748G
The indole nucleus as a selective COX-2 inhibitor and anti-inflammatory agent (2011–2022)
Anti-inflammatory bioactivity of diversely substituted indole derivatives, mainly N-1 and C-3 substituted indoles.
Org. Chem. Front., 2022,9, 3624-3639
https://doi.org/10.1039/D2QO00534D
State of knowledge in photoredox-catalysed direct difluoromethylation
The combination of visible light photoredox catalysis with direct difluoromethylation has allowed the synthesis of a large choice of CF2H-containing value-added molecules under very mild reaction conditions.
Org. Chem. Front., 2022,9, 3598-3623
https://doi.org/10.1039/D2QO00551D
Cutting edge of diphenyl phosphorazidate (DPPA) as a synthetic reagent – A fifty-year odyssey
Recent developments of diphenyl phosphorazidate (DPPA, (C6H5O)2P(O)N3) has been reviewed.
Org. Chem. Front., 2022,9, 3360-3391
https://doi.org/10.1039/D2QO00403H
Recent progress in rare-earth metal-catalyzed sp2 and sp3 C–H functionalization to construct C–C and C–heteroelement bonds
The review presents rare-earth metal-catalyzed C(sp2/sp3)–H functionalization accessing C–C/C–heteroatom bonds and olefin (co)polymerization, highlighting substrate scope, mechanistic realization, and origin of site-, enantio-/diastereo-selectivity.
Org. Chem. Front., 2022,9, 3102-3141
https://doi.org/10.1039/D1QO01859K
Recent advances in the reactions of silacyclobutanes and their applications
This review summarizes the growing landscape in the reactions of silacyclobutanes (SCBs) by highlighting fascinating progress, deconstructing mechanistic underpinnings, and drawing insight from related ring-opening and expanding reactions of SCBs.
Org. Chem. Front., 2022,9, 2840-2855
https://doi.org/10.1039/D2QO00410K
Organic dyes supported on silicon-based materials: synthesis and applications as photocatalysts
The most important advance in photocatalysis in the last decade has been the synthesis and application of organic compounds to promote this process.
Org. Chem. Front., 2022,9, 2856-2888
https://doi.org/10.1039/D1QO01751A
Recent advances in the catalytic asymmetric construction of atropisomers by central-to-axial chirality transfer
We highlighted the recent advances in the field of central-to-axial chirality transfer for the synthesis of axially chiral molecules.
Org. Chem. Front., 2022,9, 2280-2292
https://doi.org/10.1039/D1QO01699G
Recent advances in transition metal-catalyzed heteroannulative difunctionalization of alkenes via C–H activation for the synthesis of heterocycles
In this review article, we summarized recent advances in the transition metal-catalyzed heteroannulative difunctionalization of alkenes via direct C–H activation to access heterocyclic frameworks.
Org. Chem. Front., 2022,9, 2256-2279
https://doi.org/10.1039/D2QO00081D
Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle
We highlighted the recent advances in the field of multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds.
Org. Chem. Front., 2022,9, 2013-2055
https://doi.org/10.1039/D1QO01749G
Recent advances in rhodium-catalysed cross-dehydrogenative-coupling between two C(sp2)–H bonds
A comprehensive review overviewing the advances in Rh-catalyzed cross-dehydrogenative-coupling in the period of 2016–2021 is presented.
Org. Chem. Front., 2022,9, 1992-2012
https://doi.org/10.1039/D1QO01948A
Chemical and chemoenzymatic stereoselective synthesis of β-nucleosides and their analogues
β-Nucleosides are fundamental building blocks of biological systems and are used as therapeutic agents for the treatment of cancer and viral infections. This review summarizes the stereoselective synthesis of β-nucleosides and their analogues.
Org. Chem. Front., 2022,9, 1719-1741
https://doi.org/10.1039/D1QO01936H
Recent advances in transition-metal catalyzed directed C–H functionalization with fluorinated building blocks
This review focuses on the advances in transition-metal catalyzed reactions with fluorinated building blocks via directed C–H bond activation for the construction of diverse organic molecules with an insight into the probable mechanistic pathway.
Org. Chem. Front., 2022,9, 1742-1775
https://doi.org/10.1039/D1QO01544C
Coordination-assisted, transition-metal-catalyzed enantioselective desymmetric C–H functionalization
Recent advances in transition-metal-catalyzed enantioselective desymmetric C–H functionalization are summarized.
Org. Chem. Front., 2022,9, 1458-1484
https://doi.org/10.1039/D1QO01884A
Visible light photocatalysis in the synthesis of pharmaceutically relevant heterocyclic scaffolds
Visible light and photoredox catalysis have emerged as a powerful and long-lasting tool for organic synthesis, demonstrating the importance of a variety of chemical bond formation methods.
Org. Chem. Front., 2022,9, 1485-1507
https://doi.org/10.1039/D1QO01602D
Recent advances in transition-metal-free trifluoromethylation with Togni's reagents
Transition-metal-free trifluoromethylations have attracted significant research interest driven by the increasing importance of CF3-containing compounds.
Org. Chem. Front., 2022,9, 1152-1164
https://doi.org/10.1039/D1QO01504D
The application of C–H bond functionalization in the total syntheses of indole natural products
The recent advances in total synthesis of indole natural products focusing on the application of C–H bond functionalization are summarized.
Org. Chem. Front., 2022,9, 1195-1210
https://doi.org/10.1039/D1QO01636A
About this collection
Critical reviews and highlight articles published in Organic Chemistry Frontiers during 2022 are collated as below for the benefit of readers.