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Themed collection New reactivity in organic chemistry

29 items
Open Access Editorial

New reactivity in organic chemistry: a themed collection

Andrei Yudin and Corinna Schindler introduce the Chemical Science themed collection on the topic of new reactivity in organic chemistry.

Graphical abstract: New reactivity in organic chemistry: a themed collection
From the themed collection: New reactivity in organic chemistry
Open Access Perspective

Catalytic hydrogen atom transfer to alkenes: a roadmap for metal hydrides and radicals

Hydrogen atom transfer from metal hydrides to alkenes appears to underlie widely used catalytic methods – the mechanistic implications are fascinating.

Graphical abstract: Catalytic hydrogen atom transfer to alkenes: a roadmap for metal hydrides and radicals
From the themed collection: 2020 Chemical Science HOT Article Collection
Open Access Perspective

Synthetic half-reactions

This perspective on reactivity introduces Synthetic Half-Reactions (SHRs) as a way to analyze chemical transformations.

Graphical abstract: Synthetic half-reactions
From the themed collection: New reactivity in organic chemistry
Open Access Perspective

Electro-organic synthesis – a 21st century technique

This perspective provides insight into recent electro-organic methods and general trends in this field, and opens up prospects for future viewpoints.

Graphical abstract: Electro-organic synthesis – a 21st century technique
From the themed collection: 2020 Chemical Science HOT Article Collection
Open Access Edge Article

Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation

Cubane has attracted attention due to its unique 3D structure. Herein, we report the programmable synthesis of multiply arylated cubanes. The developed reaction allows the late-stage and regioselective installation of aryl groups.

Graphical abstract: Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations

The venerable Hauser–Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. A catalytic Hauser–Kraus annulation has been developed based on N-heterocyclic carbene catalysis.

Graphical abstract: N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C–N/C–O-forming cascade

An intramolecular C(sp3)–H amidation proceeds in the presence of t-BuOK, molecular oxygen, and DMF.

Graphical abstract: Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C–N/C–O-forming cascade
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights

The selective 1,2-aminoacylation of olefins provides opportunities for the rapid construction of nitrogen-containing molecules.

Graphical abstract: Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Effect of the enamine pyramidalization direction on the reactivity of secondary amine organocatalysts

Endo-pyramidalisation at nitrogen bestows enamines derived from α-substituted amines with higher reactivity compared to exo-pyramidalisation.

Graphical abstract: Effect of the enamine pyramidalization direction on the reactivity of secondary amine organocatalysts
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Brønsted acid catalysis of photosensitized cycloadditions

Brønsted acids can catalyze triplet energy transfer reactions, and DFT computations suggest the unexpected importance of reorganization energy for catalysis.

Graphical abstract: Brønsted acid catalysis of photosensitized cycloadditions
From the themed collection: New reactivity in organic chemistry
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
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

Studies of S-linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O-glycoside counterparts.

Graphical abstract: Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

The oxidative coupling of alkyltrifluoroborates with heteroatom-tethered vinylarenes leads to a broad range of saturated oxygen and nitrogen heterocycles.

Graphical abstract: Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines
From the themed collection: New reactivity in organic chemistry
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
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol

In this manuscript, we describe the conversion of fuscol, a natural product isolated in 1978, to xishacorenes A, B, and C, isolated in 2017, as well as a previously unreported congener, which we have named xishacorene D.

Graphical abstract: Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

Through rational evaluation of ligands and promoters, the reactivity of a key Pd(II) species towards transmetalation or β-H elimination is manipulated.

Graphical abstract: A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

Chiral phosphoric acid catalyzed the formal [4+2]-cycloaddition of 2-benzothiazolimines with enecarbamates to provide benzothiazolopyrimidines with up to 99% yield and >99% ee.

Graphical abstract: Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines
From the themed collection: New reactivity in organic chemistry
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
From the themed collection: New reactivity in organic chemistry
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
From the themed collection: New reactivity in organic chemistry
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
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis

Synthetic chemists have spent considerable effort optimizing the synthesis of nitrogen and oxygen containing compounds through a number of methods; however, direct introduction of N- and O-functionality remains challenging.

Graphical abstract: Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Metal-free alkene oxy- and amino-perfluoroalkylations via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides

A practical metal-free perfluoroalkylation using acid anhydrides with unique reaction mode via carbocation has been developed.

Graphical abstract: Metal-free alkene oxy- and amino-perfluoroalkylations via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Catalyst-dependent selectivity in sulfonium ylide cycloisomerization reactions

An unusual example of π-acid catalyst-dependent selectivity in the cycloisomerization of alkene-tethered sulfonium ylides affords cyclopropanes or dihydrofurans with excellent control of chemoselectivity.

Graphical abstract: Catalyst-dependent selectivity in sulfonium ylide cycloisomerization reactions
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Reversibly tuning hydrogel stiffness through photocontrolled dynamic covalent crosslinks

By controlling the stability of dynamic covalent crosslinks with adjacent photoswitches, the stiffness of an adaptable hydrogel is tuned reversibly.

Graphical abstract: Reversibly tuning hydrogel stiffness through photocontrolled dynamic covalent crosslinks
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy

A novel regio- and stereocontrolled macrocyclization strategy was developed for the first synthesis of ceanothine D.

Graphical abstract: Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity

Replacing the O-linked saccharide in the bacteriocin glycocin F with an S-linked version results in a peptidomimetic that increases the bacteriostatic effect.

Graphical abstract: Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles

Ni-catalysed diarylation of vinylpyridylsilanes with arylzinc reagents and aryl halides is reported by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles.

Graphical abstract: Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Mechanistic insights on the Pd-catalyzed addition of C–X bonds across alkynes – a combined experimental and computational study

A mechanistic study of the Pd-catalyzed intramolecular addition of carbamoyl chlorides and aryl halides across alkynes is presented.

Graphical abstract: Mechanistic insights on the Pd-catalyzed addition of C–X bonds across alkynes – a combined experimental and computational study
From the themed collection: New reactivity in organic chemistry
Open Access Edge Article

Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters

An enantioselective, redox-relay Heck alkenylation of trisubstituted allylic alkenol substrates has been developed.

Graphical abstract: Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters
From the themed collection: New reactivity in organic chemistry
29 items

About this collection

Associate Editor Professor Andrei K. Yudin and Guest Editor Professor Corinna Schindler introduce this themed collection on the topic of new reactivity in organic chemistry. This collection is made up of a selection of previously published Edge content that has been carefully selected by Andrei and Corinna, to showcase what they feel represents new reactivity in organic chemistry around the topics of metal catalysis, difunctionalisation, strained ring systems, C-H functionalisation, oxidation, photochemistry, fluorination, organocatalysis, and biomolecule and natural product synthesis. This collection also features some specially curated review content on the topics of electro-organic synthesis, metal hydride hydrogen atom transfer, and synthetic half-reactions.

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