A visible-light-mediated decarboxylative coupling reaction of phenylacetic acid derivatives, featuring sulfur hexafluoride (SF) as the oxidant, has been developed. This metal-free method allows for the synthesis of a series of bibenzyl derivatives and complex all-carbon skeletons, facilitating efficient utilization and degradation of the greenhouse gas SF.
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Visible-light-induced decarboxylative cyclization.
Org Biomol Chem
December 2024
Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India.
The application of visible light as an energy source provides a new avenue in organic transformation due to its mildness, efficiency and selectivity. In fact, recent years have witnessed remarkable advances in photoinduced decarboxylative coupling reactions involving carboxylic acids and their derivatives. Under appropriate photoredox conditions they undergo single electron transfer (SET), resulting in reactive radicals which can assemble with suitable reaction partners.
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Int J Mol Sci
December 2024
Institute of Translational Biomedicine, St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034, Russia.
Currently, the TAAR1 receptor has been identified in various cell groups in the intestinal wall. It recognizes biogenic amine compounds like phenylethylamine or tyramine, which are products of decarboxylation of phenylalanine and tyrosine by endogenous or bacterial decarboxylases. Since several gut bacteria produce these amines, TAAR1 is suggested to be involved in the interaction between the host and gut microbiota.
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Org Lett
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Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, South Korea.
Enamides have emerged as robust alternatives for enamines, exhibiting versatile reactivity for further synthetic modifications, including nucleophilic addition, cycloaddition, and asymmetric hydrogenation. While transition-metal-catalyzed cross-coupling of alkenyl (pseudo)halides with amides has been widely employed to construct this valuable scaffold, it suffers from some limitations, such as the need for transition-metal catalysts and the preparative synthesis of alkenyl (pseudo)halides. In this study, we report a mild and convenient stereoretentive decarboxylative amidation of α,β-unsaturated carboxylic acids with easily procurable 1,4,2-dioxazol-5-ones, providing a practical synthetic route to enamides.
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Org Lett
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College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China.
We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr(BF) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.
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Nat Chem
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Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan.
The biosynthesis of the lincosamide antibiotics lincomycin A and celesticetin involves the pyridoxal-5'-phosphate (PLP)-dependent enzymes LmbF and CcbF, which are responsible for bifurcation of the biosynthetic pathways. Despite recognizing the same S-glycosyl-L-cysteine structure of the substrates, LmbF catalyses thiol formation through β-elimination, whereas CcbF produces S-acetaldehyde through decarboxylation-coupled oxidative deamination. The structural basis for the diversification mechanism remains largely unexplored.
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