“Deficient” but “efficient”, the first example of catalytic Friedel-Crafts alkylation of arenes, carrying electron-withdrawing groups, with alcohols is reported. The optmized iron(III) chloride (97%) FeCl3 catalyzed allylation, benzylation and propargylation procedures opened access to a range of tetrahydro-naphthalenes, tetrahydro-isoquinolines and tetrahydro-benzo[d]azepines featuring tertiary benzylic stereocenters in excellent yields (up to 92%) and short reaction time.
M. Bandini, M. Tragni, A. Umani-Ronchi (2009). Iron(III)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Electron-Deficient Arenes with pi-Activated Alcohols. ADVANCED SYNTHESIS & CATALYSIS, 351, 2521-2524 [10.1002/adsc.200900441].
Iron(III)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Electron-Deficient Arenes with pi-Activated Alcohols
BANDINI, MARCO;TRAGNI, MICHELE;UMANI RONCHI, ACHILLE
2009
Abstract
“Deficient” but “efficient”, the first example of catalytic Friedel-Crafts alkylation of arenes, carrying electron-withdrawing groups, with alcohols is reported. The optmized iron(III) chloride (97%) FeCl3 catalyzed allylation, benzylation and propargylation procedures opened access to a range of tetrahydro-naphthalenes, tetrahydro-isoquinolines and tetrahydro-benzo[d]azepines featuring tertiary benzylic stereocenters in excellent yields (up to 92%) and short reaction time.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
