Journal of Molecular Catalysis A-Chemical, Vol.283, No.1-2, 140-145, 2008
Heck-type reactions of allylic alcohols - Part IV: (2-Substituted)-1-indanones via 5-endo-trig cyclizations
Various conditions have been tested to obtain efficiently 2-methyl-1-indanone via the Pd-catalyzed 5-endo-trig cyclization of 1-(o-bromophenyl)2-methylprop-2-en-1-ol. High yield (97%) was obtained at 120 degrees C in DMF with Pd(OAc)(2)/cinchonine as the catalytic system and NaHCO3 as the base. Use of this procedure for the synthesis of other substituted indanones led to lower yields but replacing thermal heating by microwave heating improved greatly the results. (c) 2007 Elsevier B.V. All rights reserved.