Copper-catalyzed C-H bond direct chalcogenation of aromatic compounds leading to diaryl sulfides, selenides, and diselenides by using elemental sulfur and selenium as chalcogen sources under oxidative conditions

Chemistry, an Asian Journal
Fumitoshi ShibaharaToshiaki Murai

Abstract

The reactions of aromatic compounds and elemental chalcogens catalyzed by a copper salt with molecular oxygen as an oxidant were carried out. The reaction of 3-substituted imidazo[1,5-a]pyridines and elemental sulfur in the presence of CuTC (copper(I) thiophenecarboxylate) gave the corresponding bisimidazopyridyl sulfides in good to quantitative yields. The reaction proceeded even under aerobic oxidation conditions. The use of a polar solvent was crucial for the reaction, and DMSO (dimethyl sulfoxide) in particular stimulated the reaction. The reaction could be applied to common aromatic compounds, such as N-methyl indole and dialkyl anilines. The reaction of indole proceeded at the nucleophilic C3 position rather than at the acidic C2 position. In addition, the reaction of dialkyl anilines proceeded with an ortho, para orientation. The reactions of imidazopyridines and elemental selenium under similar conditions gave the corresponding bisimidazopyridyl diselenides along with bisimidazopyridyl monoselenides. The resulting diselenides were readily converted to the corresponding monoselenides with unreacted imidazopyridines under the same conditions. The reaction could be applied to the copolymerization of bifunctional bisimidazo...Continue Reading

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Citations

Feb 4, 2014·Chemistry : a European Journal·Masayuki IwasakiYasushi Nishihara
May 27, 2015·Organic & Biomolecular Chemistry·Vutukuri Prakash ReddyNobuaki Kambe
Jan 31, 2015·Chemical Communications : Chem Comm·Ke YangHongjian Lu
Apr 29, 2016·Chemistry : a European Journal·Gianpiero Cera, Lutz Ackermann
Aug 5, 2016·The Journal of Organic Chemistry·Lin MinHuayue Wu
Aug 18, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Masayuki Iwasaki, Yasushi Nishihara
Jul 21, 2016·Angewandte Chemie·Tobias GenschFrank Glorius
Jun 27, 2017·Chemical Communications : Chem Comm·Jun-Rong ZhangRi-Yuan Tang
Apr 29, 2020·Organic & Biomolecular Chemistry·Ana Maria S RecchiGilson Zeni
Aug 26, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Deepika YadavSatish Kumar Awasthi
May 24, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Daniel S RamponDiego Alves
Jan 18, 2018·Organic & Biomolecular Chemistry·Sumbal SabaAntonio L Braga
Dec 2, 2014·The Journal of Organic Chemistry·Renhua QiuNobuaki Kambe
Apr 26, 2019·The Journal of Organic Chemistry·Thiago J PeglowDiego Alves
Sep 11, 2014·Organic Letters·Masayuki IwasakiYasushi Nishihara

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