Themed collection 2020 Organic Chemistry Frontiers Review-type Articles
Nickel-catalyzed enantioselective electroreductive cross-couplings
Ni-Catalyzed reductive cross-coupling of two electrophiles has evolved into a powerful means for building diverse carbon-carbon bonds in an enantioselective manner. Here we summarize the recent progress in Ni-catalyzed enantioselective electroreductive coupling reactions.
Tailoring radicals by asymmetric electrochemical catalysis
We highlight asymmetric electrochemical catalysis as a powerful tool in facilitating radical transformations. The tunable features of electrochemical methods enable mild generations of radicals and provide control of chemo- and stereoselectivity.
Organic micro/nanoscale materials for photonic barcodes
This review summarizes recent advances in micro/nanoscale photonic barcodes based on organic materials from the aspects of diverse optical encoding techniques.
Photoinduced strategies towards strained molecules
Photoinduced strategies towards radical reactions of [1.1.1]propellane and bicyclo [1.1.0]butanes by photoredox or metallaphotoredox catalysis have recently been disclosed, enabling controllable construction of 1,3-difunctionalized bicyclo[1.1.1]pentanes and cyclobutanes.
Recent advances in phosphoranyl radical-mediated deoxygenative functionalisation
Alcohols and carboxylic acids have been established as versatile building blocks in the assembly of various carbon frameworks.
Dual N-heterocyclic carbene/photocatalysis: a new strategy for radical processes
Dual N-heterocyclic carbene/photocatalysis displays unique features compared with the traditional methods and indicates high potential for new radical processes.
Recent advances in photoelectrochemical cells (PECs) for organic synthesis
The application of PECs in organic synthesis reactions and their reaction mechanisms are highlighted.
Recent applications of biphotonic processes in organic synthesis
Organic synthesis mediated by biphotonic processes has gained great momentum in the last five years. Herein, an overview of the existing examples is reported.
Aromatization-driven deconstruction/refunctionalization of unstrained rings
Aromatization-driven ring-opening/functionalization of common unstrained rings has been developed with the in situ generation of pre-aromatic fused spiro heterocycles as the key step.
Merging photochemistry with electrochemistry in organic synthesis
Recent advances merging photochemistry with electrochemistry in organic synthesis are highlighted.
Solid phase synthesis in the development of magnetic resonance imaging probes
We review the use of the solid phase synthesis methodology for the preparation of diverse and potent MRI probes.
Industrial synthesis of reactive silicones: reaction mechanisms and processes
Silicones are used in many applications, from consumer products to medicinal and electronic devices. In this review we describe the most relevant reactions and industrial processes to furnish them, focusing specially on OH-terminated polysiloxanes.
The present and future synthetic strategies of structural modifications of sinomenine
This review summarizes the modifications of sinomenine, a hot compound derived from herbal plants, which possesses diverse biological activities and low cytotoxicity.
The same oxygenation-state introduction of hypervalent sulfur under transition-metal-free conditions
This review discusses the application of the same oxygenation-state introduction of hypervalent sulfur strategy under transition-metal-free conditions.
Ni-Catalyzed stereoselective difunctionalization of alkynes
We summarize the progress of the nickel-catalyzed alkyne difunctionalization reaction for the synthesis of tri- and tetrasubstituted olefins, with an emphasis on the strategy and control of stereochemistry.
Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives
This review summarizes the progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives and their applications in total synthesis of natural products, and gives some insights into challenging issues in this research field.
New frontiers in the transition-metal-free synthesis of heterocycles from alkynoates: an overview and current status
This review highlights the successful utilization of transition-metal-free approaches for the modular assembly of various heterocycles from alkynoates.
Recent developments in dehydration of primary amides to nitriles
Various dehydration methods available for the direct conversion of amides to the corresponding nitriles have been reviewed.
Construction of all-carbon quaternary stereocenters by catalytic asymmetric conjugate addition to cyclic enones in natural product synthesis
This review discusses the construction of all-carbon quaternary stereocenters using catalytic asymmetric conjugate addition and its application in natural product synthesis.
Stay positive: catalysis with 1,3,2-diazaphospholenes
Fundamental properties and recent advances in the catalytic application of 1,3,2-diazaphospholenes are reviewed, and future directions for the field are presented.
Recent advances in transition metal migration involving reactions
In this review, various types of metal-migration involved methodologies, including palladium, rhodium, iron, cobalt, iridium, chromium, nickel, platinum, are summarized and demonstrated elaborately for giving a better access to this field.
Asymmetric catalytic construction of fully substituted carbon stereocenters using acyclic α-branched β-ketocarbonyls: the “Methyl Rule” widely exists
This review illustrates the recent advances in catalytic asymmetric α-functionalization of acyclic β-ketocarbonyls. A thorough survey of all these reactions indicates the existance of a general principle which is called the “Methyl Rule”.
A diversity of recently reported methodology for asymmetric imine reduction
This review describes recent developments in enantioselective imine reduction, including related substrates in which a CN bond is the target for reduction, and in situ methods.
The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products
The first review article summarizing known methodologies for the preparation of (4H)-imidazol-4-ones and their application in the total synthesis of imidazol-4-one containing natural products.
Recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions
In this review, we summarized recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions.
Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes
This review highlights recent progress in tandem selenocyclization and tellurocyclization with alkenes and alkynes, with an emphasis on the scopes, limitations and mechanisms of these different reactions.
Recent advances in the synthesis of bridgehead (or ring-junction) nitrogen heterocycles via transition metal-catalyzed C–H bond activation and functionalization
An update on recent advances in the synthesis of bridgehead nitrogen fused heterocycles via transition metal-catalyzed C–H activation and functionalization is reported.
Recent advances in the synthesis of xanthones and azaxanthones
A useful chemical toolbox for (aza)xanthones from 2012 to 2020 that covers the optimization of known procedures and novel methodologies.
Recent progress in the usage of tetrabromo-substituted naphthalenetetracarboxylic dianhydride as a building block to construct organic semiconductors and their applications
The recent synthetic strategies and significant applications of TBNDA and their derivatives as promising building blocks to construct π-expanded semiconductors have been carefully summarized in this review.
Enzymatic and non-enzymatic crosslinks found in collagen and elastin and their chemical synthesis
This review summarized the enzymatic and non-enzymatic crosslinks found in collagen and elastin and their organic synthesis.
Organoselenium chemistry-based polymer synthesis
Novel synthesis of selenium containing polymers with pre-determined structures and applications thereof.
Cavity-based applications of metallo-supramolecular coordination cages (MSCCs)
This review describes cavity-based applications of cage-like SCCs such as molecular recognition and separation, stabilization of reactive species by encapsulation, as drug delivery systems and as molecular flasks.
Recent advances in nitro-involved radical reactions
Significant progress in the chemistry of nitro radicals has been witnessed in the past decades, providing efficient and rapid access to nitro-containing compounds. This review describes recent advances in nitro-involved radical reactions, and summarizes various transformations.
Advances in the catalytic asymmetric synthesis of quaternary carbon containing cyclobutanes
The advances in the catalytic asymmetric synthesis of quaternary carbon containing cyclobutanes are described.
Promising reagents for difluoroalkylation
This review describes recent advances in difluoroalkylation reactions using different substrates.
Recent advances in metal catalyzed or mediated cyclization/functionalization of alkynes to construct isoxazoles
This review summarized the recent developments in metal catalyzed or mediated cyclization/functionalization of alkynes to construct isoxazoles.
Radical reactions promoted by trivalent tertiary phosphines
The background and recent breakthroughs in the single-electron-transfer (SET) reactions with trivalent tertiary phosphines are summarized and discussed in detail, and an outlook in the developments within this field is provided.
Light-mediated olefin coordination polymerization and photoswitches
This review outlines photoswitchable, transition metal-based olefin coordination polymerization catalysts ranging from homogeneous to heterogeneous, and monometallic to bimetallic regimes.
One-electron oxidative dehydrogenative annulation and cyclization reactions
This review focuses on the recent advances in one-electron oxidation involved oxidative dehydrogenative annulations and cyclizations for the intermolecular and intramolecular construction of valuable ring structures.
Recent advances in cyclization reactions of unsaturated oxime esters (ethers): synthesis of versatile functionalized nitrogen-containing scaffolds
We summarized recent advances in cyclization reactions of unsaturated oxime esters (ethers), which provide diversiform functionalized nitrogen-containing scaffolds.
Recent progress in the synthesis of limonoids and limonoid-like natural products
Recent progress in syntheses of limonoids and limonoid-like natural products is reviewed. The current “state-of-art” advance on novel synthetic strategy are summarized and future outlook will be presented.
Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)
In this review, we provide a comprehensive overview of recent progress in this rapidly growing field by summarizing the 1,6-conjugate addition and annulation reactions of p-QMs with consideration of their mechanisms and applications.
Cross-dehydrogenative coupling involving benzylic and allylic C–H bonds
Benzylic and allylic C–H bonds are coupled with C(sp)–H, C(sp2)–H and C(sp3)–H bonds in a straightforward and high atom-economic manner.
Transition metal-catalyzed coupling of heterocyclic alkenes via C–H functionalization: recent trends and applications
Heterocyclic alkenes and their derivatives are an important class of reactive feedstock and valuable synthons. This review highlights the transition-metal-catalyzed coupling of heterocyclic alkenes via a C–H functionalization strategy.
Recent developments in palladium-catalyzed C–S bond formation
This review summarized the recent developments in palladium-catalyzed C–S bond formation involving sulfenylation and sulfonylation reactions.
Cooperative photoredox and chiral hydrogen-bonding catalysis
Chiral hydrogen-bonding catalysis is a classic strategy in asymmetric organocatalysis. Recently, it has been used to cooperate with photoredox catalysis, becoming a powerful tool to access optical pure compounds via radical-based transformations.
Anthranils: versatile building blocks in the construction of C–N bonds and N-heterocycles
This review article provides an overview of the recent progress in the transformations of anthranils, which have emerged as versatile building blocks in the assembly of various C–N bonds and medicinally active heterocyclic systems.
Chelation-assisted transition metal-catalysed C–H chalcogenylations
This review summarizes recent advances in C–S and C–Se formations via transition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.
Recent progress in C(aryl)–C(alkyl) bond cleavage of alkylarenes
Cleavage of the C(aryl)–C(alkyl) σ-bond is important both in academy and industry as it holds the potential to provide straightforward access to a variety of targets from readily available chemical feedstocks such like alkylarenes.
Trifluoroacetimidoyl halides: a potent synthetic origin
In the review, recent advances in the synthetic applications of trifluoroacetimidoyl halides have been summarized.
Recent advances in the synthesis of indoles from alkynes and nitrogen sources
This review highlights ten years of success in the synthesis of indoles using alkynes and nitrogen sources as substrates.
Recent advances in the total synthesis of cyclobutane-containing natural products
Recent developments of strategies on the construction of cyclobutanes and their application in complex natural product synthesis are discussed.
About this collection
Critical reviews and highlight articles published in Organic Chemistry Frontiers during 2020 are collated as below for the benefit of readers.