Ethers are high value organic compounds widely applied in chemical industry, natural products, material, pharmaceuticals, argochemicals, as well as modern organic synthesis. Herein, we report an adaptive TFA-catalyzed cross-coupling of alcohols with various oxygen nucleophiles (nitro-, halogen-, sulfur-, nitrogen-, aryl-, and alkynyl-substituted aliphatic alcohols), delivering diverse unsymmetrical ethers under mild conditions and simple operation. This protocol features a broad range of substrate scope and high catalytic efficiency (54 examples, up to 99% yield). The decagram scale performance and one-step synthesis of drug molecules evidenced the potential industrial production and practicability of this protocol.
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http://dx.doi.org/10.1186/s13065-025-01379-4 | DOI Listing |
BMC Chem
January 2025
The Affiliated Ganzhou Hospital, Jiangxi Medical College, Nanchang University, Ganzhou, 341000, Jiangxi, People's Republic of China.
Natl Sci Rev
January 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials, Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM), National Engineering Laboratory for Green Chemical Productions of Alcohols, Ethers and Esters, College of Chemistry and Chemical Engineering, Xiamen University, China.
J Phys Chem A
January 2025
Advanced Computational Chemistry Centre, Cotton University, Guwahati 781001, India.
The complete conversion of dinitrogen to ammonia mediated by a side-on N-bound carbene-beryllium complex, [NHC-Be(η-N)] has been studied considering both the symmetric and unsymmetric pathways. -heterocyclic carbenes complexed with Be(η-N) moieties were considered substrates in our study. We found that two mechanistic pathways were possible for the reduction of dinitrogen to form ammonia.
View Article and Find Full Text PDFChemistry
December 2024
Department of Applied Chemistry for Environment, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo, 192-0397, Japan.
We report the physical properties of a new class of triarylmethyl-based carbocations containing both an electron-donating diphenyl ether moiety and an electron-accepting carbonyl group with a helical plane framework. Their unique packing patterns were clarified by X-ray crystallographic analysis, which depend on the counter anions to influence their photophysical properties in the solid states. Notably, the interactions between π-cation species and planar anion species lead to a unique panchromatic property, accompanying a near-infrared absorption with a λ value of 1030 nm, which can be assigned to intermolecular charge transfer transition.
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.
Herein, we report the efficient intramolecular dehydrative coupling of symmetrical and unsymmetrical diols for the synthesis of macrocyclic crown ethers in the presence of Ni-zeolite as a catalyst under continuous flow module. This method is also efficient for the intramolecular dehydrative macrolactonization of seco-acids using Ni-zeolite or Ru-zeolite. This flow catalysis is demonstrated by a wide substrate scope with one-time packed Ni-zeolite to produce 20 macrocyclic polyethers and 11 examples of broad macrolactones with water as a byproduct.
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