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In light of the small ring strain of five/six-membered cyclic ethers, constructing complex molecules via ring-opening reactions has consistently been a highly challenging topic in organic synthesis. Induced by Lewis acids, the charge redistribution in cyclic ethers forms oxonium ylide intermediates, thereby activating the C–O bond and subsequently facilitating nucleophilic attack for ring opening. In recent years, a variety of novel Lewis acids, encompassing those with new metal centers and frustrated Lewis pairs (FLPs), have been effectively utilized to induce the formation of oxonium ylides, offering a diverse array of methods for the ring opening of five/six-membered cyclic ethers. This review conveys the extensive application advancements of diverse Lewis acid types for cyclic ether ring-opening reactions over the past two decades, originating from the perspective of the classification of Lewis acids. Furthermore, the substrate applicability and chemical transformation efficiency of these Lewis acids in the ring-opening reactions of cyclic ethers have also been discussed herein. [ABSTRACT FROM AUTHOR]

A novel fluorescent probe containing an imine structure was synthesized through a condensation reaction based on the skeleton of antipyrine. Due to the synergistic effect of photoinduced electron transfer (PET), excited-state intramolecular proton transfer (ESIPT), and E/Z isomerization, the probe itself has weak fluorescence. When zinc ions are added to the ethanol solution of the probe, the formed complex inhibits PET, ESIPT, and E/Z isomerization while activating chelation-enhanced fluorescence (CHEF), resulting in fluorescent "turn-on" at 462 nm. Under optimal detection conditions, the probe can rapidly respond to zinc ions within 3 min, with a linear range of 60–220 μM and a lower limit of detection (LOD) of 0.63 μM. It can also specifically identify zinc ions in the presence of 13 common metal ions. [ABSTRACT FROM AUTHOR]

In this work, we developed a visible‐light‐driven method for the selective synthesis of amides and N‐acylureas from carboxylic acids and thioureas. This protocol was featured as avoidance of additional oxidants and transition metal catalysts, simple manipulations, low cost, broad substrate scope, and good functional group tolerance. As only oxygen serves as the oxidation reagent, this method provides a promising synthesis candidate for the formation of N‐aryl amides and N‐acylureas, including late‐stage functionalization of complex pharmaceutical molecules and biologically active molecules. [ABSTRACT FROM AUTHOR]

An iron-catalyzed selective N=S coupling of N -methoxy amides and sulfoxides has been developed and was found to be a highly efficient method for the synthesis of N -acyl sulfoximines. Electron-donating as well as electron-withdrawing groups on the phenyl ring are tolerated, and even sensitive substituents are compatible. The current catalytic transformation was conducted under an air atmosphere and can be easily scaled up to a gram scale with a catalyst loading of only 1 mol %. In this case, both coupling partners are used in their native forms, thus obviating prior functionalization and activation., Competing Interests: The authors declare no competing financial interest., (© 2024 The Authors. Published by American Chemical Society.)