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Themed collection Carbenes in Organic Synthesis

14 items
Review Article

Recent developments in photochemical reactions of diazo compounds

Chemistry of diazo compounds is dominated by transition metal catalysis but recently, photoinitiated reactions of diazo compounds have attracted a lot of attention. This mini-review describes recent discoveries on the reactivity of diazo compounds under light irradiation.

Graphical abstract: Recent developments in photochemical reactions of diazo compounds
From the themed collection: Synthetic methodology in OBC
Review Article

Catalytic carbene/alkyne metathesis (CAM): a versatile strategy for alkyne bifunctionalization

Cascade reactions involving a catalytic carbene/alkyne metathesis (CAM) process through a vinyl carbene intermediate provide an efficient and step-economic approach for the construction of polycyclic frameworks with structural diversity.

Graphical abstract: Catalytic carbene/alkyne metathesis (CAM): a versatile strategy for alkyne bifunctionalization
From the themed collection: Synthetic methodology in OBC
Accepted Manuscript - Communication

α-Thiocarbonyl Synthesis via FeII-Catalyzed Insertion Reaction of α-Diazocarbonyls into S–H Bonds

From the themed collection: Carbenes in Organic Synthesis
Communication

Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes

The catalytic asymmetric synthesis of mono-fluoro-, -chloro- and -bromomethyl-1,2-diaryl ester cyclopropanes is described.

Graphical abstract: Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes
From the themed collection: Catalysis & biocatalysis in OBC
Communication

Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides

Wittig-type reactivity between iodosoarenes and phosphoranes leads to monocarbonyl iodonium ylides, which readily serve as metallocarbene precursors.

Graphical abstract: Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides
From the themed collection: Carbenes in Organic Synthesis
Communication

Cp*Co(III)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds

Cp*Co(III)-catalysed selective alkylation of directed C–H bonds of arenes and heteroarenes has been accomplished employing donor–acceptor carbenes, derived from α-diazocarbonyl compounds.

Graphical abstract: Cp*Co(iii)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds
From the themed collection: Carbenes in Organic Synthesis
Communication

Iron-catalysed carbene-transfer reactions of diazo acetonitrile

Herein we report the flow synthesis of hazardous diazo acetonitrile to enable X–H insertion reactions with a readily available iron catalyst.

Graphical abstract: Iron-catalysed carbene-transfer reactions of diazo acetonitrile
From the themed collection: Carbenes in Organic Synthesis
Accepted Manuscript - Paper

Understanding exo-selective Diels-Alder reactions involving Fischer-type carbene complexes

From the themed collection: Carbenes in Organic Synthesis
Paper

[RhIII(Cp*)]-catalyzed arylfluorination of α-diazoketoesters for facile synthesis of α-aryl-α-fluoroketoesters

The Cp*Rh(III)-catalyzed cascade arylfluorination reactions of α-diazoketoesters with arylboronic acids and N-fluorobenzenesulfonimide for one-pot C(sp3)–C(aryl) and C(sp3)–F bond formation was achieved.

Graphical abstract: [RhIII(Cp*)]-catalyzed arylfluorination of α-diazoketoesters for facile synthesis of α-aryl-α-fluoroketoesters
From the themed collection: Carbenes in Organic Synthesis
Paper

Copper(I)-carbenes as key intermediates in the [3 + 2]-cyclization of pyridine derivatives with alkenyldiazoacetates: a computational study

This work reports a computational study of the copper(I)-catalyzed regioselective synthesis of indolizine derivatives through the [3 + 2]-cyclization reaction of vinyldiazo acetates and pyridine derivatives.

Graphical abstract: Copper(i)-carbenes as key intermediates in the [3 + 2]-cyclization of pyridine derivatives with alkenyldiazoacetates: a computational study
Paper

Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

The generation of novel 1,2,5-oxathiazole-S-oxide cycloadducts from cycloaddition of nitrile oxide dipoles with α-oxo sulfines generated in situ from α-diazosulfoxides is reported.

Graphical abstract: Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines
From the themed collection: Synthetic methodology in OBC
Paper

Intramolecular trapping of ammonium ylides with N-benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold

The present work documents an operationally simple, clean and practical method for accessing the 2,2-disubstituted indolin-3-one (pseudoindoxyl) scaffold.

Graphical abstract: Intramolecular trapping of ammonium ylides with N-benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold
From the themed collection: Synthetic methodology in OBC
Paper

Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents

A simple protocol to directly access γ-amino acid derivatives by intermolecular regioselective hydroamination of trichloroethyl alkenyldiazoacetates with carbamate using a silver tetrafluoroborate catalyst is described.

Graphical abstract: Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents
From the themed collection: Carbenes in Organic Synthesis
Paper

In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

Herein, a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite, was developed effectively to give fully substituted isoxazoles.

Graphical abstract: In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles
From the themed collection: Carbenes in Organic Synthesis
14 items

About this collection

This themed collection, Guest Edited by Professor Anita Maguire, Professor Michael Doyle and Professor Jianbo Wang, highlights the latest developments in the field of carbenes as reactive intermediates or catalysts in organic synthesis. The collection includes new reactions and synthetic methodologies based on carbenes, asymmetric catalysis in carbene reactions, the application of carbenes in natural product synthesis, the application of carbenes in chemical biology, and experimental and computational analyses of the reaction mechanisms of carbene transformations.

Articles in this themed collection will be added below as soon as possible after they are published.

Please return to this page frequently to see the collection grow.

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