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Introducing fluorine into organic compounds enables their electronic properties to be tuned and can also significantly alter their function. Now, the α-fluorination of amides has been achieved using nucleophilic fluorinating agents using a polarity reversal strategy. This new method has been used to synthesize a fluorinated analogue of the blockbuster antidepressant drug, citalopram.

1,4-Dicarbonyls are challenging targets owing to the natural-polarity mismatch of potential reaction partners. This Review discusses methods for 1,4-dicarbonyl synthesis based on the coupling of two carbonyl-containing fragments as well as methods that involve non-carbonyl precursors. A spotlight on 1,4-dicarbonyls in total synthesis underlines the diversity of approaches for this motif.

We introduce a method for the direct 1,3-difunctionalization of alkenes, based on a concept termed ‘charge relocation’, which enables stereodivergent access to 1,3-difunctionalized products of either syn- or anti-configuration from unactivated alkenes.

The rapid assembly of complex scaffolds in a single step from simple precursors would be an ideal reaction in terms of efficiency and sustainability. Now, the single-step construction of alkaloid-like frameworks from three dynamically assembled precursors has been reported. Using a dual-catalytic system, the transformation involves a hydride shuttle process initiated by a hydride donation event.

Classical hydroacylation of alkenes with aldehydes is a straightforward route to ketones, however aldehyde decarbonylation is a common side-process. Here, the authors report the coupling of amides, as hydroacylating agents, and alkenes under mild, metal-free conditions to afford a wide range of ketones.

To mark the occasion of Nature Chemistry turning 10 years old, we asked scientists working in different areas of chemistry to tell us what they thought the most exciting, interesting or challenging aspects related to the development of their main field of research will be — here is what they said.

The discovery of immunosuppressive natural products and synthetic strategies to make these compounds have impacted biology and ultimately human health. This Review highlights synthetic examples of such compounds, which have the potential to discover immunological mechanisms.

Nitrogen containing heterocycles play key roles as both bioactive compounds and synthetic building blocks in organic chemistry. Here, the authors report the synthesis of a range of heterocyclic structures via metal free cycloadditions and provide mechanistic analyses for the transformations.

Alkenes are versatile buildings blocks in organic synthesis. Here, the authors developed a three-membered ring strategy to access a variety of functionalized alkenes by coupling of in-situ generated azines with sulfoxonium ylides.

Crosslinking mass spectrometry (XL-MS) has become a crucial tool for studying protein structures and interactions in their native environments, however, the current cleavable linkers are fraught with practical limitations. Here, the authors synthesize and characterize DiSPASO, a novel lysine-reactive, MS-cleavable, and membrane-permeable crosslinker with an alkyne-based click chemistry handle for affinity enrichment, showing potential for improving protein-protein interaction mapping.