Themed collection 2022 Organic Chemistry Frontiers Review-type Articles
Organogermanium(IV) compounds in photo-induced radical reactions
Behaviors of typical organogermanium(IV) compounds in photo-induced reactions are reviewed.
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.
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.
Recent developments in enantioselective nickel(II)-catalyzed conjugate additions
This review updates the field of enantioselective nickel-catalyzed conjugate additions since 2016.
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.
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.
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.
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.
Recent developments in calixpyrrole (C4P)-based supramolecular functional systems
Recent advances with calixpyrrole-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.
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.
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.
An overview of the applications of chiral phosphoric acid organocatalysts in enantioselective additions to CO and CN 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.
Radical coupling reactions of hydrazines via photochemical and electrochemical strategies
Hydrazines are versatile building blocks in organic synthesis.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
The synthesis of seven- and eight-membered rings by radical strategies
Radical strategies for preparation of seven- or eight-membered rings.
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.
Radical addition to the CC 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.
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.
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).
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Coordination-assisted, transition-metal-catalyzed enantioselective desymmetric C–H functionalization
Recent advances in transition-metal-catalyzed enantioselective desymmetric C–H functionalization are summarized.
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.
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.
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.
About this collection
Critical reviews and highlight articles published in Organic Chemistry Frontiers during 2022 are collated as below for the benefit of readers.