Themed collection Most popular 2021 organic chemistry articles, 2021

Fundamental progress, current developments, and rapidly growing applications of iminoboronate and salicylhydroxamic–boronate conjugate esters are deliberated.

A review that highlights water as the logical reaction medium in which organic chemistry can be practiced. The key roles that water can play in directing reaction outcomes, including impacting mechanistic features, are discussed using selected examples.

Among numerous solvents available for chemical transformations, 1,1,1,3,3,3-hexafluoro-2-propanol (popularly known as HFIP) has attracted enough attention of the scientific community in recent years.

Transition metal-catalysed functionalizations of inert C–H bonds to construct C–C bonds represent an ideal route in the synthesis of valuable organic molecules.

In the presence of the bulky monophosphine P^tBu₃, palladium usually prefers to react with Ar–Cl over Ar–OTf bonds. However, strongly coordinating solvents can bind to palladium, inducing a reversal of selectivity.

Unveiling the immune fingerprint of MOFs: the design of customized immune-active MOF nanoplatforms for targeting specific diseases will open new avenues for their biomedical applications.

Galbofloxacin, a novel theranostic xenosiderophore antibiotic, exhibits unparalleled potency in combating S. aureus infections in vivo.

Enantioselective palladaelectro-catalyzed C–H alkenylations and allylations were achieved by the means of an easily-accessible amino acid for the synthesis of N–C axially chiral indole biaryls.

Enantiodivergence is an important concept in asymmetric catalysis that enables access to both enantiomers of a product relying on the same chiral source as reagent.

In the race to find efficient singlet fission materials, picking a winner is not easy. Femtosecond stimulated Raman spectroscopy can help us choose the best candidates, as demonstrated here in choosing from a library of rubrene derivatives.

The electron-withdrawing group at the meso-position of Thio-Cy5 could dramatically reduce the singlet–triplet energy gap, and speed up the intersystem crossing process.

2-Chloromethyl acryl derivatives (acrylamides and acrylates) can serve as simple and versatile bioconjugation reagents to achieve site-selective cysteine and disulfide modification on demand and with high efficiency.

Generation of fluoromethyl radicals via visible light-mediated halogen atom transfer activation of fluoroiodomethane facilitates both the multicomponent synthesis of α-fluoromethyl amines and the hydrofluoromethylation of electron-deficient alkenes.

Halogen-atom transfer (XAT) based on phosphoranyl radical chemistry enables the hydroxymethylation of alkyl iodides with formaldehyde.

This work explores divergent reactivity of the benzylic gem-boron–silicon and boron–tin double nucleophiles, including the arylation of the C–B bond with Ar–Cl, along with a complementary oxidative λ³-iodane-guided arylation of the C–Si/Sn moiety.

1,2-Dicarbonyl compounds with FDA-approved sweeteners as leaving groups deliver CO for protection against acute kidney injury in mice.

Alkene 1,2-dicarbofunctionalizations increase molecular complexity. Herein, the carboallylation, carboalkenylation, carboalkynylation, and carboarylation of olefins is accomplished through radical/polar crossover with organotrifluoroborates.

A simple and scalable method for stereoselective synthesis of thioethers directly from alcohols using isothiouronium salts is presented. The utility of this thiol-free reaction was exemplified by late-stage modification of complex molecules.

A Ni-catalyzed enantioselective reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. A MLR model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.

A nickel-catalyzed reductive asymmetric aryl-allylation of tethered unactivated alkenes has been developed, providing diverse benzene-annulated cyclic compounds bearing a quaternary stereocenter with high regio-, E/Z- and enantio-selectivity.

Divergent reactions of sulfinates with pyridinium salts were developed by controlling the one- versus two-electron reaction manifolds.

Sulfonamides are now accessible directly from carboxylic acids by a one-step, tricomponent decarboxylative amidosulfonation that provides the missing link between the two key functionalities.

Complex N-alkyl (heteroaryl)onium salts are accessed via heterocyclic group transfer reactions of N-ligated I(iii) reagents with alkenoic acids. The reactions proceed in excellent yields, under mild conditions, and with broad substrate scope.

Prodrug activation strategy by utilizing the reaction between aryl azide and endogenous acrolein that is generally overproduced by cancer cells.

This works demonstrates the implementation of an electron donor–acceptor (EDA) complex platform toward Ni-catalyzed C(sp³)–C(sp²) bond formation, circumventing the need for exogenous photocatalysts, additives, and stoichiometric metal reductants.

A CPL intensity of up to 3 × 10⁻² is achieved in π-extended 6-helicene derivatives, owing to an intense helicene-mediated exciton coupling. Corresponding top-emission CP-OLEDs afforded a promising g_El of around 8 × 10⁻³.

Acenes in the Greek cross (+) stack orientation exhibit selective hole and electron transfer coupling based on gerade symmetry in frontier molecular orbitals.

A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed.

Lewis acid mediated activation enables mild, metal-free, and highly functional group tolerant C–H aminoalkylation of diverse azoles via three-component coupling.

Thiol-reactive inhibitors for the cellular entry of cyclic oligochalcogenide (COC) transporters and SARS-CoV-2 spike pseudo-lentivirus are reported.