ChemInform Abstract: Synthesis of Triaryls: Hydroxy and Amine Dinaphthyl and Diphenanthryl Aryls by One-Pot Electron-Transfer Nucleophilic Substitution Reactions

Autor: Natalia Vanesa Torres, Adriana B. Pierini, José L. Borioni, Liliana B. Jimenez
Rok vydání: 2014
Předmět:
Zdroj: ChemInform. 45
ISSN: 0931-7597
DOI: 10.1002/chin.201445107
Popis: A new one-pot synthetic route to achieve the preparation of hydroxy and amine binaphthyl and biphenanthryl aryls is here reported. This approach involves the reaction of 1,4-bromoiodobenzene, 4,4′-diiodobiphenyl, and 1,4- and 1,5-diiodonaphthalene with the anions of 2-naphthylamine, 2-naphthol, and 9-phenanthrylamine under irradiation in liquid ammonia. The reactions proceed to afford triaryl derivatives in moderate to good yields (∼45% of 1,4-phenylene- and 1,4-naphthylene-1,1′-dinaphthalen-2-ols as well as 1,4-phenylene-1,1′-dinaphthalen-2-amine and 10,10′-diphenanthren-9-amine). Lower yields (27%) of polyaryl derivatives are obtained by reaction of 4,4′-diiodobiphenyl with anions of 2-naphthol and 9-phenanthrylamine.
Databáze: OpenAIRE