PERSONAL DE APOYO
TORRES Natalia Vanesa
artículos
Título:
Synthesis of triaryls: hydroxy and amine dinaphthyl and diphenanthryl aryls by one-pot electron-transfer nucleophilic substitution reactions
Autor/es:
LILIANA B. JIMENEZ; NATALIA TORRES; JOSE L. BORIONI; ADRIANA B. PIERINI
Revista:
TETRAHEDRON
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Lugar: Amsterdam; Año: 2014 vol. 70 p. 3614 - 3620
ISSN:
0040-4020
Resumen:
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, 4,40-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-1,10-dinaphthalen-2-ols as well as 1,4-phenylene-1,10-dinaphthalen-2-amine and 1,10-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.