Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one

The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using KF as base, DMF as solvent and Pd(OAc)(2) as catalyst, the target products were obtained in moderate to good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromopyridines can also be employed. (C) 2008 Elsevier Ltd. All rights reserved.