The palladium(O)-catalyzed annulation of catechol with propargylic carbonates, bearing different functionalized groups (hydroxy, tertbutyldimethylsilyloxy, ester, diethylamino) afforded functionalized 2,3-dihydro-2-ylidene-1,4-benzodioxin isomers. The regioselectivity of the cyclization depends strongly on the nature of the substituent and on the chain length between the triple bond and the function. (c) 2006 Elsevier B.V. All rights reserved.