INQUISUR   21779
INSTITUTO DE QUIMICA DEL SUR
Unidad Ejecutora - UE
artículos
Título:
Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes
Autor/es:
LO FIEGO, MARCOS J.; SILBESTRI, GUSTAVO F.; LOCKHART, MARIA T.; CHOPA, ALICIA B.
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Editorial:
AMER CHEMICAL SOC
Referencias:
Año: 2011 vol. 76 p. 1707 - 1714
ISSN:
0022-3263
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 AlCl3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.