Themed collection Most popular 2019-2020 organic chemistry articles

30 items
Open Access Perspective

C–H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals

Intramolecular and intermolecular HAT to C-centered radicals enables selective C–H functionalization of organic molecules.

Graphical abstract: C–H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals
Open Access Perspective

New avenues for C–B bond formation via radical intermediates

Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary to existing transition-metal catalysed cross coupling processes.

Graphical abstract: New avenues for C–B bond formation via radical intermediates
Open Access Perspective

A synthetic chemist's guide to electroanalytical tools for studying reaction mechanisms

A range of electroanalytical tools can be applied to studying redox reactions, probing key mechanistic questions in synthetic chemistry.

Graphical abstract: A synthetic chemist's guide to electroanalytical tools for studying reaction mechanisms
Open Access Perspective

Toward ideal carbon dioxide functionalization

From carbon fixation, Grignard reaction, metal-catalyzed reactions and asymmetric CO2-incorporation, what would be the ideal CO2-functionalization?

Graphical abstract: Toward ideal carbon dioxide functionalization
Open Access Edge Article

Allylic C(sp3)–H alkylation via synergistic organo- and photoredox catalyzed radical addition to imines

A new catalytic method for the direct alkylation of allylic C(sp3)–H bonds from unactivated alkenes via synergistic organo- and photoredox catalysis is described.

Graphical abstract: Allylic C(sp3)–H alkylation via synergistic organo- and photoredox catalyzed radical addition to imines
Open Access Edge Article

N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts

By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts.

Graphical abstract: N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts
Open Access Edge Article

Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles

Here we report palladium-catalyzed, regiodivergent [5 + 4] and [5 + 2] annulations of vinylethylene carbonates and allylidenemalononitriles affording over 50 medium-sized heterocycles in high isolated yields with excellent regioselectivities.

Graphical abstract: Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles
Open Access Edge Article

Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis

Formyl-selective deuteration of aldehydes with D2O mediated by the synergistic combination of light-driven, polyoxometalate-facilitated HAT and thiol catalysis is reported.

Graphical abstract: Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis
Open Access Edge Article

Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)–H arylation

Pd-catalyzed ligand-enabled γ-C(sp3)–H arylation of tert-leucine and its derived peptides without using an external directing group via a less favored six-membered palladacycle is reported.

Graphical abstract: Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)–H arylation
Open Access Edge Article

Sulfamides direct radical-mediated chlorination of aliphatic C–H bonds

Amine-anchored sulfamides direct radical-mediated chlorination of aliphatic C–H bonds. The site of C–H abstraction can be modulated by varying the sulfamide nitrogen substituents, a feature that has not been demonstrated with other substrate classes.

Graphical abstract: Sulfamides direct radical-mediated chlorination of aliphatic C–H bonds
Open Access Edge Article

Secondary amine selective Petasis (SASP) bioconjugation

Secondary amine selective Petasis (SASP) bioconjugation for the selective labeling of peptides and proteins with N-terminal secondary amines.

Graphical abstract: Secondary amine selective Petasis (SASP) bioconjugation
Open Access Edge Article

Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation

We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres.

Graphical abstract: Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
Open Access Edge Article

Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes

The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations.

Graphical abstract: Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes
Open Access Edge Article

Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry

The first general solid-state Suzuki–Miyaura cross-coupling reactions using mechanochemistry has been developed.

Graphical abstract: Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
Open Access Edge Article

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades

A divergent strategy for the remote arylation, vinylation and alkylation of nitriles is described.

Graphical abstract: A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades
Open Access Edge Article

Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source

The well-known [(TAML)Fe(OH2)] complex undergoes proton-coupled oxidation to an Fe-oxo species that supports electrochemical C–H oxidation and alcohol dehydrogenation.

Graphical abstract: Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source
Open Access Edge Article

Rhodium catalyzed template-assisted distal para-C–H olefination

We report first example of template assisted rhodium catalyzed para-C–H alkenylation.

Graphical abstract: Rhodium catalyzed template-assisted distal para-C–H olefination
Open Access Edge Article

Trifluoromethylthiolation–arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling

Multicomponent reaction of diazocarbonyl and dibenzenesulfonimide-SCF3 reagents with BAr4 salts in the presence of Zn(NTf2)2 gives α,α′-difunctionalized trifluoromethylthio compounds.

Graphical abstract: Trifluoromethylthiolation–arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling
Open Access Edge Article

Diacetyl as a “traceless” visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions

Minisci alkylation is of prime importance for its applicability in functionalizing diverse heteroarenes, which are core structures in many bioactive compounds.

Graphical abstract: Diacetyl as a “traceless” visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions
Open Access Edge Article

Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium

A general and practical method to directly convert phenols into primary anilines with cheap and easy-to-handle hydrazine as the amine and hydride sources catalyzed by Pd/C.

Graphical abstract: Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium
Open Access Edge Article

Primary α-tertiary amine synthesis via α-C–H functionalization

A reactive ketimine intermediate was demonstrated to be intercepted by a variety of nucleophiles including organometallics and TMSCN.

Graphical abstract: Primary α-tertiary amine synthesis via α-C–H functionalization
Open Access Edge Article

Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride

Herein, we report the radiosynthesis of 18F-difluoromethylarenes via the assembly of three components, a boron reagent, ethyl bromofluoroacetate, and cyclotron-produced non-carrier added [18F]fluoride.

Graphical abstract: Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride
Open Access Edge Article

Catalytic β C–H amination via an imidate radical relay

An iodine-catalyzed strategy for β C–H amination of alcohols is enabled by a chemo-, regio-, and stereo-selective H-atom transfer mechanism.

Graphical abstract: Catalytic β C–H amination via an imidate radical relay
Open Access Edge Article

Enabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines

A nanogram-to-gram workflow has been established for the identification and development of synthetic transformations which are enabling in Fragment-Based Drug Discovery (FBDD). In this study, we disclose a method for the synthesis of privileged sp2–sp3 architectures via direct cross-dehydrogenative coupling of heterocycles.

Graphical abstract: Enabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines
Open Access Edge Article

A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A

A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed and applied to the synthesis of (+)-rumphellaone A.

Graphical abstract: A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A
Open Access Edge Article

Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.

Graphical abstract: Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant
Open Access Edge Article

δ C–H (hetero)arylation via Cu-catalyzed radical relay

A radical relay strategy has been developed to enable selective δ C–H arylation. The approach employs a chiral copper catalyst, which serves the dual roles of generating an N-centered radical to promote intramolecular H-atom transfer, and then intercepting a distal C-centered radical for C–C bond formation with (hetero)aryl boronic acids.

Graphical abstract: δ C–H (hetero)arylation via Cu-catalyzed radical relay
Open Access Edge Article

Photoredox-mediated remote C(sp3)–H heteroarylation of free alcohols

We report an efficient and economical method for remote δ C(sp3)–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis.

Graphical abstract: Photoredox-mediated remote C(sp3)–H heteroarylation of free alcohols
Open Access Edge Article

Rhodium(II)-catalyzed C–H aminations using N-mesyloxycarbamates: reaction pathway and by-product formation

DFT study to elucidate the mechanism of Rh-catalyzed C–H aminations with N-mesyloxycarbamates and the pathway by which by-products formed.

Graphical abstract: Rhodium(ii)-catalyzed C–H aminations using N-mesyloxycarbamates: reaction pathway and by-product formation
Open Access Edge Article

Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base.

Graphical abstract: Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
30 items

About this collection

This specially curated collection pulls together some of the most popular articles from 2019 and 2020 in the field of organic chemistry. The collection presents some outstanding contributions to the field, ranging from electroanalytical tools for studying reaction mechanisms through to C-H functionalisation methodology, and as with all Chemical Science articles – they are all completely free to access and read. We hope you enjoy browsing through this collection.

See also:

Most popular 2019-2020 inorganic, main group and crystal engineering chemistry articles
Most popular 2019-2020 materials and energy chemistry articles
Most popular 2019-2020 physical and theoretical chemistry articles
Most popular 2019-2020 catalysis articles
Most popular 2019-2020 analytical chemistry articles
Most popular 2019-2020 supramolecular chemistry articles
Most popular 2019-2020 chemical biology articles
Most popular 2019-2020 review articles

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