Synthesis of triaryls: hydroxy and amine dinaphthyl and diphenanthryl aryls by one-pot electron-transfer nucleophilic substitution reactions

LILIANA B. JIMENEZ, NATALIA V. TORRES, JOSÉ L. BORIONI, ADRIANA B. PIERINI

TETRAHEDRON

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2014 vol. 70 p. 3614 - 3620

0040-4020

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 (w45% of 1,4-phenylene- and 1,4-naphthylene-1,10-dinaphthalen-2-ols as well as 1,4-phenylene-1,10-dinaphthalen-2-amine and 10,100-diphenanthren-9-amine). Lower yields (27%) of polyaryl derivatives are obtained by reaction of 4,40-diiodobiphenyl with anions of 2-naphthol and 9-phenanthrylamine.