Themed collection Most popular 2018-2019 organic chemistry articles

Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary to existing transition-metal catalysed cross coupling processes.

A range of electroanalytical tools can be applied to studying redox reactions, probing key mechanistic questions in synthetic chemistry.

This Perspective article traces the evolution of modern approaches to functionalise the indole C4–H bond.

Mechanochemistry is becoming more widespread as a technique for molecular synthesis with new mechanochemical reactions being discovered at increasing frequency. This perspective explores what more it can offer, aside from the clear benefit of reduced solvent consumption.

Multicomponent reactions promoted by mechanical energy are critically reviewed.

This review explores the different synthetic methods by which dispersity and MWD shape can be tuned and discusses the different properties and applications where this variation is beneficial.

The utilization of physical organic molecular descriptors for the quantitative description of reaction outcomes in multivariate linear regression models is demonstrated as an effective tool for a priori prediction and mechanistic interrogation.

The application of exo-type directing groups (DGs) has led to the discovery of a wide range of novel C(sp³)–H activation methods, which allow efficient and site-selective functionalization of alcohol and amide derivatives.

We report a redox-neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction.

A method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry.

Two prominent trifluoromethylation reagent classes join forces in a bench stable hypervalent iodosulfoximine CF₃ transfer agent. We report its synthesis, properties and reactivity, opening up new possibilities in trifluoromethylation chemistry.

A divergent strategy for the remote arylation, vinylation and alkylation of nitriles is described.

Minisci alkylation is of prime importance for its applicability in functionalizing diverse heteroarenes, which are core structures in many bioactive compounds.

A general and practical method to directly convert phenols into primary anilines with cheap and easy-to-handle hydrazine as the amine and hydride sources catalyzed by Pd/C.

Photoredox-mediated alkylation of heteroaryl sulfones under redox-neutral, acid-free conditions to create drug-like molecules.

BODIPY as an EWG in asymmetric catalysis is presented.

A reactive ketimine intermediate was demonstrated to be intercepted by a variety of nucleophiles including organometallics and TMSCN.

We report direct amination of electron-poor arenes and evaluate the crucial factors for the enhanced reactivity in hexafluoroisopropanol.

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.

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.

We report an efficient and economical method for remote δ C(sp³)–H heteroarylation of free aliphatic alcohols using a hypervalent iodine PFBI-OH oxidant under photoredox catalysis.

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B₂(OH)₄ reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base.

Reported herein is a novel, useful, visible light-promoted ring-opening functionalization of unstrained cycloalkanols.

A substrate-directed approach to couple alkylzinc nucleophiles, alkyl halide electrophiles, and non-conjugated alkenes under nickel catalysis is described.

Aryldiazoacetates can undergo photolysis under blue light irradiation (460–490 nm) at room temperature and under air in the presence of numerous trapping agents, such as styrene, carboxylic acids, amines, alkanes and arenes, thus providing a straighforward and general platform for their mild functionalization.

Aromatic acids are converted into aryl bromides simply and efficiently via decarboxylation providing new depth and insight into Hunsdiecker-type reactivity.

Direct access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety was achieved via a palladium-catalysis.

An operationally simple, metal-free protocol for regioselective halogenation of a range of 8-substituted quinolines has been established using recyclable trihaloisocyanuric acids.

An interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade allows the direct and metal free dual vicinal functionalisation of heterocycles. For example, C3 thio, C2 allyl indoles are prepared in one synthetic operation from the union of the parent indoles and allyl sulfoxides.

We present herein a nickel-catalyzed dicarbofunctionalization of alkenes using readily available organoboronic acids and organic halides in a three-component fashion.