13867-27-1Relevant academic research and scientific papers
Metal- and Phenol-Free Synthesis of Biaryl Ethers: Access to Dibenzobistriazolo-1,4,7-oxadiazonines and Vancomycin-Like Glyco-Macrocycles as Antibacterial Agents
Singh, Kartikey,Sharma, Gaurav,Shukla, Manjulika,Kant, Ruchir,Chopra, Sidharth,Shukla, Sanjeev K.,Tripathi, Rama P.
, p. 14882 - 14893 (2018/12/14)
An efficient synthesis of biaryl ethers, from electron-deficient aryl halides using NaH/DMSO under metal- and phenol-free conditions, has been achieved to access dibenzo-bistriazolo-1,4,7-oxadiazonines and vancomycin-like glyco-macrocycles. A 44-membered glyco-macrocycle showed promising activity against vancomycin-resistant Staphylococcus aureus (VRSA).
Method for the preparation of diphenyl ether compounds
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Paragraph 0053-0055, (2016/12/01)
The invention relates to a method for preparing a diphenyl ether compound. The method is characterized by comprising the following technical steps of: (1) adding a halogenated benzene derivative and a bis(pinacolato)diboron into a reaction vessel, adding copper chloride or aluminum chloride and 1,2-bi(diphenylphosphine) ethane as a catalyst, then adding alkaline and an organic solvent, and reacting at 25-160 DEG C for 6-24 hours; and (2) after extracting a reaction solution obtained from the step (1) by using ethyl acetate, purifying by a 200-300 meshes silica gel column, pre-eluting the silica gel column by using 20-50 mL of normal hexane, eluting by adopting an eluent at a flow speed of 1-2 mL/min for 3-6 hours, and removing the solvent to obtain the diphenyl ether compound. The method for preparing the diphenyl ether compound, disclosed by the invention, no only overcomes the disadvantage of the use of phenolic substances in a reaction process, but also has the advantages of mild reaction condition and high yield.
Palladium-catalysed and phosphine-promoted synthesis of diaryl ethers through self-coupling
Wang, Dawei,Xu, Zhaojun,Yu, Xiaoli,Li, Yongliang,Wan, Huida
, p. 691 - 693 (2016/11/18)
An efficient, palladium acetate-catalysed, tributylphosphine-promoted direct synthesis of symmetrical diaryl ethers through the self-coupling of aryl fluorides has been developed with K2CO3/ZrO2 as a base. This provides an alternative method to prepare aromatic polymers, important synthetic intermediates and natural products for use in the field of pharmaceuticals and industrial materials.
Iridium-catalyzed synthesis of diaryl ethers by means of chemoselective C-F bond activation and the formation of B-F bonds
Chen, Jianping,Zhao, Keyan,Ge, Bingyang,Xu, Chongying,Wang, Dawei,Ding, Yuqiang
supporting information, p. 468 - 473 (2015/02/05)
Transition-metal-catalyzed C-F activation, in comparison with C-H activation, is more difficult to achieve and therefore less fully understood, mainly because carbon-fluorine bonds are the strongest known single bonds to carbon and have been very difficult to cleave. Transition-metal complexes are often more effective at cleaving stronger bonds, such as C(sp2)-X versus C(sp2)-X. Here, the iridium-catalyzed C-F activation of fluorarenes was achieved through the use of bis(pinacolato)diboron with the formation of the B-F bond and self-coupling. This strategy provides a convenient method with which to convert fluoride aromatic compounds into symmetrical diaryl ether compounds. Moreover, the chemoselective products of the C-F bond cleavage were obtained at high yields with the C-Br and C-Cl bonds remaining.
