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Themed collection HOT articles in Organic Chemistry Frontiers in 2016

40 items
Research Article

Synthesis of a figure-eight azahelicene dimer with high emission and CPL properties

A bisbutadiyne bridged azahelicene dimer with a figure-eight shape, which exhibited both high fluorescence quantum yield and CPL properties, has been synthesized through the Glaser–Hay homo-coupling reaction with diethynylazahelicene.

Graphical abstract: Synthesis of a figure-eight azahelicene dimer with high emission and CPL properties
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Mechanism of selective C–H cyanation of 2-phenylpyridine with benzyl nitrile catalyzed by CuBr: a DFT investigation

The mechanism of C–H cyanation of 2-phenylpyridine with 2-phenylacetonitrile catalyzed by the CuBr catalyst was elaborated based on DFT calculations.

Graphical abstract: Mechanism of selective C–H cyanation of 2-phenylpyridine with benzyl nitrile catalyzed by CuBr: a DFT investigation
Research Article

New reactivity of ethynyl benziodoxolone: modulating iron-catalyzed dehydration of propargyl alcohols

This is the first example of using only a catalytic amount of silyl-EBX in a dehydration reaction since its discovery. Preliminary mechanistic studies ruled out the radical pathways and supported an E1 process.

Graphical abstract: New reactivity of ethynyl benziodoxolone: modulating iron-catalyzed dehydration of propargyl alcohols
Research Article

The stability and reactivity of tri-, di-, and monofluoromethyl/methoxy/methylthio groups on arenes under acidic and basic conditions

The stability and reactivity of tri-, di- and monofluoromethyl groups under acidic and basic conditions are described.

Graphical abstract: The stability and reactivity of tri-, di-, and monofluoromethyl/methoxy/methylthio groups on arenes under acidic and basic conditions
Open Access Research Article

Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates

The title compounds, including the parent 3-azido-2H-azirine, were generated by low-temperature photolysis of the corresponding 1,1-diazidoethenes, and characterised not only by trapping reactions, but also by direct detection using NMR and in situ IR spectroscopy.

Graphical abstract: Direct observation and characterisation of 3-azido-2H-azirines: postulated, but highly elusive intermediates
Research Article

Copper-mediated annulation of 2-(1-arylvinyl) anilines and aryl nitrosos towards 2,3-diaryl-2H-indazoles

A copper-mediated annulation of 2-(1-substituted vinyl)anilines and aryl nitrosos is developed, giving 2,3-diaryl pyrazoles in moderate to good yields.

Graphical abstract: Copper-mediated annulation of 2-(1-arylvinyl) anilines and aryl nitrosos towards 2,3-diaryl-2H-indazoles
Research Article

The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition was developed, which provides a straightforward and efficient pathway to highly functionalized free pyrrolidine β-amino acids.

Graphical abstract: The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition
Research Article

Suzuki coupling for preparation of allenes – ligand effects and chirality transfer

o-(Diphenylphosphino)benzaldehyde has been identified as the effective ligand for the coupling of propargylic carbonates and organoboronic acids under mild conditions.

Graphical abstract: Suzuki coupling for preparation of allenes – ligand effects and chirality transfer
Research Article

Rh(I)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion

A Rh(I)-catalyzed cross-coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols has been successfully achieved.

Graphical abstract: Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion
Research Article

[2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines

A carbene precursor plays a dual role as both an organocatalyst and as a ligand for the copper catalyst in asymmetric silylation.

Graphical abstract: [2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines
Research Article

Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

A highly efficient manganese-catalysed hydroperoxidation of carbon–carbon double bonds of enynes as well as styrene derivatives using N-hydroxyphthalimide, N-hydroxybenzotriazole or N-hydroxysuccinimide was developed.

Graphical abstract: Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions
Research Article

A new approach toward the synthesis of 2,4-bis(fluoroalkyl)-substituted quinoline derivatives using fluoroalkyl amino reagent chemistry

The present work describes the unprecedented use of Fluoroalkyl Amino Reagents (FARs) to afford 2,4-bis(fluoroalkyl)-substituted quinoline derivatives in two steps under mild reaction conditions, in good yields and with a very good regioselectivity.

Graphical abstract: A new approach toward the synthesis of 2,4-bis(fluoroalkyl)-substituted quinoline derivatives using fluoroalkyl amino reagent chemistry
Research Article

Iterative catalyst controlled diastereodivergent synthesis of polypropionates

Polypropionates are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification.

Graphical abstract: Iterative catalyst controlled diastereodivergent synthesis of polypropionates
Research Article

Synthesis of 2,3-dihydrobenzofurans via the palladium catalyzed carboalkoxylation of 2-allylphenols

A new Pd-catalyzed alkene carboalkoxylation strategy for the preparation of 2,3-dihydrobenzofurans is described.

Graphical abstract: Synthesis of 2,3-dihydrobenzofurans via the palladium catalyzed carboalkoxylation of 2-allylphenols
Research Article

Switching between intermolecular and intramolecular reactions using flow microreactors: lithiation of 2-bromo-2′-silylbiphenyls

Switching between the intermolecular reaction and the intramolecular reaction was achieved at will using flow microreactors.

Graphical abstract: Switching between intermolecular and intramolecular reactions using flow microreactors: lithiation of 2-bromo-2′-silylbiphenyls
Research Article

Considering organic mechanisms and the optimization of current flow in an electrochemical oxidative condensation reaction

Careful consideration of the chemical mechanism for an oxidative condensation reaction led to improved current flow for the electrolysis.

Graphical abstract: Considering organic mechanisms and the optimization of current flow in an electrochemical oxidative condensation reaction
Research Article

Catalytic asymmetric direct-type 1,4-addition reactions of simple esters

Catalytic asymmetric 1,4-addition reactions of simple esters have been developed. The desired reactions proceeded smoothly with high enantioselectivities.

Graphical abstract: Catalytic asymmetric direct-type 1,4-addition reactions of simple esters
Research Article

Rhodium/copper-cocatalyzed annulation of benzylamines with diazo compounds: access to fused isoquinolines

Benzylamines undergo C–H activation and aerobic coupling with diazo compounds, leading to the synthesis of fused isoquinolines. This occurs via a mild synergistic rhodium- and copper-catalyzed process.

Graphical abstract: Rhodium/copper-cocatalyzed annulation of benzylamines with diazo compounds: access to fused isoquinolines
Research Article

Hyperbranched supramolecular polymer constructed from twisted cucurbit[14]uril and porphyrin via host–guest interactions

A novel supramolecular polymer was constructed between Q[14] host and 5,10,15,20-tetrakis(N-butyl-4-pyridinium)porphyrin tetrabromide guest depending on the host–guest interactions, representing the first cucurbit[14]uril-involved host–guest supramolecular polymer.

Graphical abstract: Hyperbranched supramolecular polymer constructed from twisted cucurbit[14]uril and porphyrin via host–guest interactions
Research Article

Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

An iterative asymmetric hydration of dienoates approach to Leucasndrolide A was explored.

Graphical abstract: Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A
Research Article

Pd(II)-catalyzed direct functionalization of C–H bonds of benzamides for synthesis of 1,1-difluoro-1-alkenes

Pd-catalyzed difluoroallylation of unactivated C(sp2)–H bonds with readily available Rf-Br reagents is described.

Graphical abstract: Pd(ii)-catalyzed direct functionalization of C–H bonds of benzamides for synthesis of 1,1-difluoro-1-alkenes
Research Article

Bismuth(III) triflate-catalysed tandem cyclisations towards complex polycyclic ethers

A series of complex polycyclic ethers have been synthesised under very mild conditions using a low catalyst loading of bismuth(III) triflate.

Graphical abstract: Bismuth(iii) triflate-catalysed tandem cyclisations towards complex polycyclic ethers
Research Article

Reaction of alkenecarboxylic acids with isocyanates via rhodium(III)-catalyzed C–H activation: a versatile route to cyclic imides

A versatile cascade route to cyclic imides via direct functionalization of the β-alkenyl C–H bond of alkenoic acids was developed.

Graphical abstract: Reaction of alkenecarboxylic acids with isocyanates via rhodium(iii)-catalyzed C–H activation: a versatile route to cyclic imides
Research Article

Stimuli-responsive supramolecular gel constructed by pillar[5]arene-based pseudo[2]rotaxanes via orthogonal metal–ligand coordination and hydrogen bonding interaction

A supramolecular polyrotaxane constructed by pillar[5]arene-based pseudo[2]rotaxanes via the incorporation of metal–ligand coordination could further self-assemble to form a stimuli-responsive supramolecular gel at high concentration.

Graphical abstract: Stimuli-responsive supramolecular gel constructed by pillar[5]arene-based pseudo[2]rotaxanes via orthogonal metal–ligand coordination and hydrogen bonding interaction
Research Article

Synthesis of trifluoromethylthiolated azacalix[1]arene[3]pyridines from the Cu(II)-mediated direct trifluoromethylthiolation reaction of arenes via reactive arylcopper(III) intermediates

Cu(II)-mediated arene C–H bond trifluoromethylthiolation with Me4NSCF3 proceeds via arylcopper(III) intermediates to produce functionalized azacalix[1]arene[3]pyridine macrocycles.

Graphical abstract: Synthesis of trifluoromethylthiolated azacalix[1]arene[3]pyridines from the Cu(ii)-mediated direct trifluoromethylthiolation reaction of arenes via reactive arylcopper(iii) intermediates
Research Article

Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions

A photochemical borylation of electron-rich aryl (pseudo)halides via a triplet aryl cation mechanism has been described.

Graphical abstract: Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions
Research Article

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

2,5-Disubstituted pyrroles are synthesized by acceptorless dehydrogenative reaction of 1,2-aminoalcohols and secondary alcohols by Pt/carbon catalyst.

Graphical abstract: Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts
Research Article

A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones

The first metal-free, initiator-free, and general photochemical perfluoroalkylation of a variety of N,N-dialkylhydrazones was developed at room temperature in the absence of any external photocatalyst.

Graphical abstract: A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones
Research Article

Catalytic asymmetric α-amination of β-keto esters and β-keto amides with a chiral N,N′-dioxide–copper(I) complex

The highly efficient asymmetric α-amination of β-keto esters and β-keto amides was realized by using a chiral N,N′-dioxide/Cu(I) complex. Under mild reaction conditions, a series of chiral α-amino dicarbonyl compounds were obtained in good result.

Graphical abstract: Catalytic asymmetric α-amination of β-keto esters and β-keto amides with a chiral N,N′-dioxide–copper(i) complex
Research Article

Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone

A series of novel chiral monophosphine ligands Xiang-Phoses were designed and have been applied to the enantioselective gold-catalyzed intermolecular [2 + 2]-cycloaddition of 3-styrylindoles 1 with N-allenyl oxazolidinone 2.

Graphical abstract: Enantioselective gold-catalyzed intermolecular [2 + 2]-cycloadditions of 3-styrylindoles with N-allenyl oxazolidinone
Research Article

Synthesis of carbamates from amines and N-tosylhydrazones under atmospheric pressure of carbon dioxide without an external base

A synthetic method to carbamates from amines and N-tosylhydrazones in the presence of 1 atm of carbon dioxide was developed.

Graphical abstract: Synthesis of carbamates from amines and N-tosylhydrazones under atmospheric pressure of carbon dioxide without an external base
Research Article

Copper(I)-catalyzed sulfonylation of (2-alkynylaryl)boronic acids with DABSO

The scaffold of benzo[b]thiophene 1,1-dioxides can be easily constructed through a copper(I)-catalyzed insertion of sulfur dioxide into (2-alkynylaryl)boronic acids. The reaction proceeds via insertion of sulfur dioxide and subsequent intramolecular 5-endo cyclization.

Graphical abstract: Copper(i)-catalyzed sulfonylation of (2-alkynylaryl)boronic acids with DABSO
Research Article

Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides

A catalyst-free aminosulfonylation through insertion of sulfur dioxide with aryl/alkyl halides enabled by photoenergy is presented. Under ultraviolet irradiation, a three-component reaction of aryl/alkyl halides, sulfur dioxide, and hydrazines proceeds under mild conditions without any metals or photo-redox catalysts.

Graphical abstract: Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides
Research Article

Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations

Diastereoselective Friedel–Crafts reactions of optically pure epoxy enolsilanes afford enantiomerically-enriched β-hydroxy-α-arylketones. Aziridinyl enolsilanes react in an analogous manner.

Graphical abstract: Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations
Research Article

Visible-light promoted intermolecular halofunctionalization of alkenes with N-halogen saccharins

A simple and efficient visible-light promoted intermolecular haloamination and haloetherification of alkenes was reported.

Graphical abstract: Visible-light promoted intermolecular halofunctionalization of alkenes with N-halogen saccharins
Research Article

Pd(II)-catalyzed β-C–H arylation of O-methyl ketoximes with iodoarenes

A Pd(II)-catalyzed selective β-arylation of O-methyl ketoximes was developed using iodoarenes as the coupling partners.

Graphical abstract: Pd(ii)-catalyzed β-C–H arylation of O-methyl ketoximes with iodoarenes
Research Article

Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines and its application in the one-step synthesis of incargranine B aglycone and seneciobipyrrolidine (I)

The Au-catalyzed tandem reaction provided simple and efficient access to spiro-dipyrroloquinolines and incargranine B aglycone and (±)-seneciobipyrrolidine (I).

Graphical abstract: Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines and its application in the one-step synthesis of incargranine B aglycone and seneciobipyrrolidine (I)
Research Article

Pd/norbornene-catalyzed sequential ortho-C–H alkylation and ipso-alkynylation: a 1,1-dimethyl-2-alkynol strategy

A palladium/norbornene-catalyzed ortho-C–H alkylation and ipso-alkynylation reaction for the synthesis of 2-alkyl-1-alkynyl arenes was reported, where the use of bulky 1,1-dimethyl-2-alkynols led to significant suppression of the formation of O-alkylation and norbornene alkynylation by-products.

Graphical abstract: Pd/norbornene-catalyzed sequential ortho-C–H alkylation and ipso-alkynylation: a 1,1-dimethyl-2-alkynol strategy
Research Article

Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates

The intramolecular aza-(4 + 3) cycloaddition reactions of in situ generated aza-oxyallylic cations and furans have been reported for the construction of medium sized hydroxamate macrocycles.

Graphical abstract: Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates
Research Article

Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis

The synthesis of strained paracyclophanes is facilitated by ortho-substitution effect on phenyl ring.

Graphical abstract: Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis
40 items

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Read some of the best research published by Organic Chemistry Frontiers in 2016. These articles are recommended by OCF referees as being of significant novelty and interest.

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