Organic chemistry articles from across Nature Portfolio

Sulfur(vi) fluoride exchange and modular diazotransfer reactions have advanced click chemistry, but their mechanisms and reactivity profiles are not well understood. Now, a computational study of these reactions provides mechanistic insights and predictive reactivity models for modular diazotransfer, facilitating the development of an easy-to-prepare and -handle diazotransfer reagent with excellent reactivity.

Enantioenriched alkyl–alkyl bonds are produced from abundant alkenes in one step via Ni-catalysed asymmetric cross-hydrodimerization. This technique overcomes the reactivity and selectivity challenges associated with coupling between two similar nucleophiles.

Nickel photoredox catalysis is often limited to electron-deficient and neutral arenes. Arylthianthrenium salts can now be used as redox-active reagents to afford general reactivity with electron-rich arenes.

The synthesis of C-glycosides relies on specially designed glycosyl donors, which are often unstable and require multi-step synthesis. Now a facile method for the synthesis of diverse C-glycosides from readily available and stable 1-deoxyglycosides has been developed. A ligand-controlled site-divergent functionalization of carbohydrates by C–H sampling/nickel-catalysed cross-coupling has also been realized.

The absence of catalytic asymmetric methods for synthesizing chiral (hetero)bicyclo[n.1.1]alkanes has hindered their application in new drug discovery. Herein the authors report an enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones using a chiral Lewis acid catalyst for the synthesis of hetero-bicyclo[3.1.1]heptane.

Distinguishing between different proteins that each bind to the same type of glycan is challenging. Here, the authors demonstrate that an enzymatically synthesised library of Lewis^x ‘glycofluoroforms’ that feature site-specific fluorination can discriminate closely related proteins.

Activation of natural gas alkanes using main-group systems typically requires heating or photo-irradiation under high atmospheric pressure with low regioselectivity. Here the authors report Lewis acid-carbene adduct activation of C–H bonds in ethane, propane and n-butane under one atmospheric pressure and at room temperature with high selectivity.

Computational analysis of competing sulfur(VI)–fluoride exchange and modular diazotransfer pathways in the reaction between primary amines and fluorosulfuryl azide reveals that diazotransfer is more kinetically and thermodynamically favoured. Predictive models are formulated by combining mechanistic analysis and structure–activity relationship studies, enabling the development of an easy-to-prepare and highly reactive diazotransfer reagent.

Sulfur(vi) fluoride exchange and modular diazotransfer reactions have advanced click chemistry, but their mechanisms and reactivity profiles are not well understood. Now, a computational study of these reactions provides mechanistic insights and predictive reactivity models for modular diazotransfer, facilitating the development of an easy-to-prepare and -handle diazotransfer reagent with excellent reactivity.

Enantioenriched alkyl–alkyl bonds are produced from abundant alkenes in one step via Ni-catalysed asymmetric cross-hydrodimerization. This technique overcomes the reactivity and selectivity challenges associated with coupling between two similar nucleophiles.

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Nickel photoredox catalysis is often limited to electron-deficient and neutral arenes. Arylthianthrenium salts can now be used as redox-active reagents to afford general reactivity with electron-rich arenes.

The enantioselective formation of Csp³–Csp³ bonds is still a substantial challenge in the synthesis of complex molecules. Now, a photocatalytic system has been developed for the enantioselective alkylation of α-amino Csp³−H bonds that promotes the generation of two different alkyl radicals, followed by their cross-coupling at a chiral nickel centre.

Site-selective acylation of remote arene C(sp²)−H bonds is achieved through N-heterocyclic carbene organocatalysis. This catalytic transformation proceeds through a nitrogen radical-mediated pathway and enables the late-stage modification of drugs, amino acids and peptides under mild conditions.