info:eu-repo/semantics/article
Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
Fecha
2011-03Registro en:
Lo Fiego, Marcos Jacinto; Silbestri, Gustavo Fabián; Chopa, Alicia Beatriz; Lockhart, María Teresa; Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes; American Chemical Society; Journal of Organic Chemistry; 76; 6; 3-2011; 1707-1714
0022-3263
CONICET Digital
CONICET
Autor
Lo Fiego, Marcos Jacinto
Silbestri, Gustavo Fabián
Chopa, Alicia Beatriz
Lockhart, María Teresa
Resumen
Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl 3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.