Themed collection Most popular organic chemistry articles

In this review, the recent advances of the application of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photoredox catalyst in the past three years (2016–2018) for various organic reactions are summarized.

Recently, sulfonylation reactions using potassium/sodium metabisulfite as the sulfur dioxide surrogate have been developed rapidly. In most cases, the transformations go through radical processes with the insertion of sulfur dioxide under mild conditions. Additionally, transition metal catalysis is applied in the reactions for the synthesis of sulfonyl-containing compounds.

Building on mechanistic perspective, the review intends to demonstrate how the uniqueness of Au-catalysts has realized a myriad of electrophilic functional group transfer reactions with the use of hypervalent iodine(III) reagents over the last decade.

This feature article will describe the selected examples of organophosphine catalysis of γ-substituent allenoates with a wide range of electrophiles to give diverse annulations.

Primary amines are one of the most predominant functional groups found in organic molecules. This review covers the most recent developments on photocatalytic deaminative strategies by using Katritzky Salts as alkyl radical reservoirs.

The aim of this feature article is to show the stereochemical versatility of the metal-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

This feature article summarizes our recent achievements in alkoxy radical-promoted C–C and C–H bond functionalization starting from free alcohols.

Recent advances in the synthesis of axially chiral biaryls via transition metal-catalysed asymmetric C–H functionalization are reported.

Photoinduced PCET meets catalysis, and the accumulation of multiple redox equivalents is of key importance.

The first visible-light-promoted direct synthesis of isoflavones following the arylation of ortho-hydroxyarylenaminones by aryl onium salts was developed.

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using NaI and PPh₃ as redox catalysts.

The first example of visible light promoted fluoroalkylation reactions initiated via noncovalent interactions between solvents and R_FI is presented.

This TFA-catalyzed [3+2] cycloaddition of organic azides with α-fluoronitroalkenes, used as synthetic surrogates of α-fluoroalkynes, provides a new route to multi-substituted fluorotriazoles with broader substrate scopes and high regioselectivity.

A metal-free cascade reaction was developed for the synthesis of indolo[1,2-a]quinoline derivatives from arylsulfonyl hydrazides and 1-(2-(arylethynyl)phenyl)indoles in the presence of TBAI/TBHP.

A simple, mild and efficient approach to access fluorinated dibenz[b,e]azepines via visible-light photoredox catalysis is presented.

N-Heterocyclic carbene (NHC) ligands effective for the cross-coupling of nitroarenes were identified.

Indane-aldehydes are formed using palladium catalysis and a transient directing group to promote intramolecular C–H functionalisation with aryl bromides.

A new, practical directed anodic C–H sulfonylation of N,N-disubstituted anilines with sodium sulfinates for producing o- or p-amino arylsulfones and diarylsulfones is described.

The not so elusive carbenoid fluoroiodomethyllithium disclosed its electrophilic nature in an unprecedented direct and stereoselective fluorocyclopropanation of allylic alcohols.

Base-assisted diazonium activation has been employed to promote gold(I)/(III) redox catalysis toward allylic oxime cyclization/aryl coupling.

The nickel-catalysed dehydrogenative coupling of 1,2-di-amino-benzene with primary alcohols and diols for the synthesis of N-heterocycles is reported. The catalytic protocol enables the transformation in up to 91% yield and generates water and hydrogen gas as byproducts.

6-O-L-Ascorbyl selenoesters, thioesters and telluroesters can be efficiently and directly prepared from L-ascorbic acid and suitable functionalised chalcogenoesters through lipase-catalysed transesterification reactions.

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. Handling of the latter can be avoided with the use of this new protocol.

The photolysis of donor–acceptor diazoalkanes in the presence of propargylic alcohols furnishes valuable, sterically demanding tetra-substituted cyclopropenes in high yield under metal-free conditions.

An efficient regioselective difunctionalization of alkenes via trifluoromethylthiolation has been accomplished employing diaryl diselenide and AgSCF₃ in the presence of BF₃·OEt₂.

An unprecedented set of efficient, economical, atom-economic and exceedingly selective I₂–DMSO-promoted methods is described for the generation of different structures.

We herein report a versatile and environmentally friendly electrochemical oxidative C–H phosphonylation protocol.

Selective synthesis of indoles and quinazolines was achieved through a precise control of C–H activation/annulation by changing additives.

New radical-triggered three-component bicyclization cascades of 2-alkynylaryldiazonium tetrafluoroborates with a sulfur dioxide surrogate DABCO·(SO₂)₂ and internal alkynes have been reported for the first time, leading to 49 examples of polycyclic sulfones with moderate to good yields.

Laser ablation in liquids has been, for the first time, employed to produce oxygen vacancy-modified CoOOH nanosheets for efficient water oxidation.

A decarboxylative radical addition/cyclization strategy was developed, by which a wide range of benzimidazo[2,1-a]isoquinoline-6(5H)-ones were prepared via reaction of 2-arylbenzoimidazoles and carboxylic acids.

Thiourea dioxide is applied as the source of sulfonyl groups for the efficient synthesis of heteroaryl sulfones and sulfonamides from heteroaryl halides under visible light irradiation. This transformation proceeds through a radical process via heteroaryl sulfinate intermediates, as supported by EPR spectroscopy and DFT calculations.

A photoredox-catalyzed sulfonylation of alkyl iodides, sulfur dioxide, and electron-deficient alkenes under mild conditions is achieved. Various functional groups including nitro, halo, acetyl, sufonyl, and pyridinyl are all tolerated under the photoredox conditions.

We herein report an electrochemical oxidative C–H/N–H cross-coupling reaction in an undivided cell.

The Yb(OTf)₃ catalyzed [3+2] cycloaddition of donor–acceptor cyclopropanes with thiourea offers an efficient route to diverse 2-amino-4,5-dihydrothiophenes.