78617-32-0Relevant academic research and scientific papers
Metal-Free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C-Se Coupling of Aryl Selenoxides with Phenols
Liu, Zhengfen,Jiang, Yonggang,Liu, Chunxiang,Zhang, Linlin,Wang, Jing,Li, Tiantian,Zhang, Hongbin,Li, Minyan,Yang, Xiaodong
, p. 7386 - 7398 (2020)
Herein, we disclose the synthesis of diaryl selenides through an unexpected C-Se coupling between aryl benzyl selenoxides and phenols. The synthetic significance of the method is that it provides a mild, rapid, and metal-free access to organoselenides in high yields with excellent functional group tolerance. This coupling of aryl benzyl selenoxides reveals a completely new reaction possibility compared with aryl sulfoxides. We also probed the reaction mechanism of this unexpected transformation through experimental studies and revealed a special Se(IV)-Se(III)-Se(II) reaction pathway.
Copper-Mediated Regioselective C-H Sulfenylation and Selenation of Phenols with Phenanthroline Bidentate Auxiliary
Kajiwara, Rikuo,Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
, p. 5915 - 5919 (2020/08/05)
A copper-mediated, phenanthroline-directed highly ortho-selective C-H sulfenylation of phenols with diaryl disulfides proceeds to form the corresponding unsymmetrical diaryl sulfides in good yield. The key to success is the introduction of a phenanthroline directing group of the bidentate-chelating nature, which is easily attachable, detachable, and even recyclable. Moreover, the same strategy is applicable to the C-H selenation, giving the diaryl selenides with high efficiency and regioselectivity.
Synthetic method for diaryl selenide
-
Paragraph 0030-0040, (2019/10/23)
The invention discloses a synthetic method for diaryl selenide, and belongs to the technical field of organic synthesis. According to the method, aryl benzyl selenium oxide or 2-pyridyl benzyl selenium oxide and a phenolic compound are dissolved in anhydr
Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications
Xiong, Xiaodong,Yeung, Ying-Yeung
, p. 4033 - 4043 (2018/05/22)
An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.
Transition-Metal-Free Selective Oxidative C(sp3)-S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides
Prasad, Ch. Durga,Sattar, Moh.,Kumar, Sangit
supporting information, p. 774 - 777 (2017/03/01)
Transition-metal-free synthetic methods have been developed for the preparation of unsymmetrical diaryl and aryl alkyl chalcogenides: sulfones, sulfides, and selenides from the sp3-C-H bond of oxindole, tetralone, arylacetamide, and aryl chalco
Oxidation of Phenols, Pyrocatechols, and Hydroquinones to ortho-Quinones using Benzeneseleninic Anhydride
Barton, Derek H. R.,Brewster, Andrew G.,Ley, Steven V.,Read, Christine M.,Rosenfeld, Moshe N.
, p. 1473 - 1476 (2007/10/02)
Benzeneseleninic anhydride has been used as a mild oxidising reagent to convert phenols into o-quinones including some examples where the p-position is unblocked.The method is limited to the production of o-quinones which are not susceptible to futher reaction.Pyrocatechols and hydroquinones can also be oxidised to the corresponding quinones in excellent yield using benzeneseleninic anhydride.
