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

JIMENEZ, L.B.; TORRES, N.V; BORIONI, J.L.; PIERINI, A.B.

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 (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). Lower yields (27%) of polyaryl derivatives are obtained by reaction of 4,4-diiodobiphenyl with anions of 2-naphthol and 9-phenanthrylamine.