ceverelst

Nature, Published online: 27 March 2024; doi:10.1038/d41586-024-00922-y

Synlett
DOI: 10.1055/s-0042-1751569

Over the past two decades, bioorthogonal chemistry has profoundly impacted various chemistry-related fields, including chemical biology and drug delivery. This transformative progress stems from collaborative efforts involving chemists and biologists, underscoring the importance of interdisciplinary research. In this Account, we present the developments in bioorthogonal chemistry within our Institute for Molecules and Materials at Radboud University. The chemistry disclosed here spans from strained alkynes and alkenes to drug release and bioconjugation strategies, mirroring the extensive scope provided by bioorthogonal chemistry. By reflecting on the chemistry originating at Radboud University, this Account emphasizes that teamwork is essential for driving significant progress in bioorthogonal chemistry.1 Introduction2 Providing BCN as a Robust Bioorthogonal Tool for Chemical Biology and Beyond3 Towards Readily Available Click-to-Release trans-Cyclooctenes4 Giving Molecules Guidance5 Next Generation of Bioconjugation Strategies: Dynamic Click Chemistry6 Conclusions
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Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany

Article in Thieme eJournals:
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Nature, Published online: 13 March 2024; doi:10.1038/d41586-024-00727-z

Paracetamol can be produced from p-hydroxybenzamide at >95 % purity in 90 % yield. Aqueous ammonia treatment of poplar or oil palm empty fruit bunches forms p-hydroxybenzamide. Under continuous processing conditions, a Hofmann rearrangement converts p-hydroxybenz-amide to p-aminophenol, then liquid/liquid extraction combined with acid/base chemistry and acetylation purifies, forms, and isolates paracetamol.

Abstract

As we work to transition the modern society that is based on non-renewable chemical feedstocks to a post-modern society built around renewable sources of energy, fuels, and chemicals, there is a need to identify the renewable resources and processes for converting them to platform chemicals. Herein, we explore a strategy for utilizing the p-hydroxybenzoate in biomass feedstocks (e. g., poplar and palm trees) and converting it into a portfolio of commodity chemicals. The targeted bio-derived product in the first processing stage is p-hydroxybenzamide produced from p-hydroxybenzoate esters found in the plant. In the second stage a continuous reaction process converts the p-hydroxybenzamide to p-aminophenol via the Hofmann rearrangement and recovers the unreacted p-hydroxybenzamide. In the third stage the p-aminophenol can be acetylated to form paracetamol, which is readily isolated by liquid/liquid extraction at >95 % purity and an overall p-hydroxybenzamide-to-paracetamol process yield of ~90 %. We explore how utilization of protecting groups alters the challenges in this process and expands the portfolio of possible products to include p-(methoxymethoxy)aniline and N-acetyl-p-(methoxymethoxy)aniline. These target compounds could become value-added renewably-sourced platform chemicals that could be used to produce biodegradable plastics, pigments, and pharmaceuticals.

Synthesis
DOI: 10.1055/a-2241-6858

This short review showcases the developing field of C–H activation reactions, with a particular focus on green catalysis through the use of environmentally friendly solvents. It evaluates the effects of these solvents on reaction outcomes, environmental aspects and general efficacy, highlighting their advantages that lead to greater selectivity, lower levels of toxicity and enhanced reaction rates. Water and biobased alternatives such as polyethylene glycols, glycerol, 2-methyltetrahydrofuran, γ-valerolactone, methanol, ethanol, p-cymene and diethyl carbonate are representative examples of such solvents. The scope of this short review encompasses studies of different methodologies, catalysts, and reaction conditions that help to develop C–H activation reactions utilizing green solvents.1 Introduction2 Water3 Polyethylene Glycols (PEGs)4 Glycerol5 2-Methyltetrahydrofuran (2-MeTHF)6 γ-Valerolactone (GVL)7 Methanol8 Ethanol9 p-Cymene10 Diethyl Carbonate11 Conclusion
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Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany

Article in Thieme eJournals:
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Publication date: April 2024

Source: Chemical Engineering Research and Design, Volume 204

Author(s): Vinicius Lima Ferreira, Marco Aurélio Suller Garcia, Donato Alexandre Gomes Aranda, Pedro Nothaft Romano