Themed collection Carbenes in Organic Synthesis
Catalytic asymmetric cycloaddition reactions of enoldiazo compounds
Review of recent advances in asymmetric catalytic cycloaddition reactions of silyl-protected enoldiazo compounds.
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.
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.
Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers
This work reports a facile annulation of anthranils with aryloxyethynes or aryl propargyl ethers to construct useful benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline frameworks, respectively.
Cyclopropane–alkene metathesis by gold(I)-catalyzed decarbenation of persistent cyclopropanes
Benzo-fused norcaradienes derived from naphthalene and phenanthrene undergo gold(I)-catalyzed cyclopropane–alkene metathesis via decarbenation.
α-Thiocarbonyl synthesis via the FeII-catalyzed insertion reaction of α-diazocarbonyls into S–H bonds
Fe(OTf)2 was used to catalyze the insertion reaction of α-diazocarbonyls into S–H bonds at 40 °C.
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.
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.
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.
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.
Understanding exo-selective Diels–Alder reactions involving Fischer-type carbene complexes
Exo-selective Diels–Alder cycloaddition reactions can be successfully achieved by the proper selection of an initial Fischer carbene complex.
[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.
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.
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.
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.
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.
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.
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.