Palladium-catalyzed cross-coupling reaction of triorganoindium reagents with propargylic esters.

Triorganoindium reagents (R₃In) react with propargylic esters under palladium catalysis via an S_N2’ rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R₃In (aryl, alkenyl, alkynyl, and methyl). When chiral, nonracemic propargylic esters are employed, the reaction takes place with high anti-stereoselectivity providing allenes with high enantiomeric excess.