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Nature Synthesis, Published online: 06 February 2024; doi:10.1038/s44160-023-00478-1

Collaboration between synthesis laboratories requires procedures that are reproducible despite differences in equipment. Now, a digital standard for automated chemical synthesis reproduces results between distinct laboratory systems almost half a world apart.

Herein, we report an approach for generating thionyl fluoride (SOF2) from the commodity chemicals thionyl chloride (SOCl2) and potassium fluoride (KF). The methodology relies on a microfluidic device that can efficiently produce and dose this toxic, gaseous reagent under extremely mild and safe conditions. Subsequently, the in situ generated thionyl fluoride is reacted with an array of structurally and electronically differing carboxylic acids, leading to the direct and efficient synthesis of highly sought-after acyl fluorides. Importantly, our investigation also highlights the inherent modularity of this flow-based platform. We demonstrate the adaptability of this approach by not only synthesizing acyl fluorides, but also directly converting carboxylic acids into a diverse array of valuable compounds such as esters, thioesters, amides, and ketones. This versatility showcases the potential of this approach for a wide range of synthetic applications, underscoring its significance in the realm of chemical synthesis.

We proposed a Minisci-type strategy for the alkylation of heterocycles with a variety of boron species under low cost and easily scale-up conditions without the use of transition-metal or organo-catalysts. The extension of this strategy to other systems will provide green approaches for the post-modifications of drug molecules and complex natural products.

Abstract

This manuscript describes a general strategy for the easily scale-up alkylation of heterocycles with a wide variety of boronic acids, boronates, and trifluoroborate salts under low-cost and simple conditions without using any transition-metal or organo-photocatalysts. The key additive of catechol plays an important role in this method which in-situ activated a variety of boron-base species to alkylboronic esters (R-BCat) with a low oxidation potential. The transformation is distinguished by a broad scope, such as drug molecules and natural products. Furthermore, the methodology proves easily scalable under standard batch conditions, enhancing its practicality and accessibility.

Nature, Published online: 23 January 2024; doi:10.1038/d41586-024-00165-x

Flavour variations are mainly the result of changes at the chromosome level, sequencing effort finds.

The spiro[3.3]heptane core, with the non-coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta-benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para-benzene). The patent-free saturated analogs obtained showed a high potency in the corresponding biological assays.

Abstract

The spiro[3.3]heptane core, with the non-coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta-benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para-benzene). The patent-free saturated analogs obtained showed a high potency in the corresponding biological assays.

Nature, Published online: 23 January 2024; doi:10.1038/d41586-024-00178-6

Wine-fermentation jars used in Georgia today hint at the properties of ancient vintages.

O-Demethylation (ODM) is a strategic tool to unlock lignin applications for drop-in and new commodity, fine & specialty chemicals.

Abstract

Lignin represents the largest aromatic carbon resource in plants, holding significant promise as a renewable feedstock for bioaromatics and other cyclic hydrocarbons in the context of the circular bioeconomy. However, the methoxy groups of aryl methyl ethers, abundantly found in technical lignins and lignin-derived chemicals, limit their pertinent chemical reactivity and broader applicability. Unlocking the phenolic hydroxyl functionality through O-demethylation (ODM) has emerged as a valuable approach to mitigate this need and enables further applications. In this review, we provide a comprehensive summary of the progress in the valorization of technical lignin and lignin-derived chemicals via ODM, both catalytic and non-catalytic reactions. Furthermore, a detailed analysis of the properties and potential applications of the O-demethylated products is presented, accompanied by a systematic overview of available ODM reactions. This review primarily focuses on enhancing the phenolic hydroxyl content in lignin-derived species through ODM, showcasing its potential in the catalytic funneling of lignin and value-added applications. A comprehensive synopsis and future outlook are included in the concluding section of this review.

Nature, Published online: 19 December 2023; doi:10.1038/d41586-023-04080-5

John Tregoning compares academia to role-playing video games as a way to discuss how the choices we make can affect the paths we take.

Using highly reactive gases is appealing for efficient organic synthesis but leads to inherent safety and processing limitations. Embracing continuous-flow technologies helps mitigating those while improving the performance of the systems. Tailored catalyst incorporation opens doors to novel reaction pathways and process intensification. Optimized mass transfer in multiphasic mixtures is key to its success, especially when solids are present.

Abstract

The use of reactive gaseous reagents for the production of active pharmaceutical ingredients (APIs) remains a scientific challenge due to safety and efficiency limitations. The implementation of continuous-flow reactors has resulted in rapid development of gas-handling technology because of several advantages such as increased interfacial area, improved mass- and heat transfer, and seamless scale-up. This technology enables shorter and more atom-economic synthesis routes for the production of pharmaceutical compounds. Herein, we provide an overview of literature from 2016 onwards in the development of gas-handling continuous-flow technology as well as the use of gases in functionalization of APIs.

Researchers turn commercial plastic into reusable monomer without solvent or extreme temperatures

Nature, Published online: 07 December 2023; doi:10.1038/d41586-023-03755-3

Scientists studying the electrical charge on coffee particles stumble on a secret to a better cup of joe.

Synthesis
DOI: 10.1055/a-2204-2801

The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining the original C–O bonds is presented. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. Combined experimental and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.
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In a year when disagreements over scientific matters like COVID-19 continue to occupy political discourse, the surfacing of a spate of high-profile research errors is regrettable. It’s crucial that the public trusts science at a time when so many topics—...

Nature, Published online: 14 November 2023; doi:10.1038/d41586-023-03552-y

The machine-learning model takes less than a minute to predict future weather worldwide more precisely than other approaches.