A versatile Pd-catalyzed intermolecular syn-carboamination of dihydrofurans giving access to the ubiquitous furoindoline motif is described. The efficiency of the process relies on the use of Buchwald-type biarylphosphines and the perfect control for site-selectivity of Pd insertion across the C═C bond. A catalytic sequence consisting of Heck and carboamination cross-coupling reactions from readily available dihydrofurans affords—in usually high chemical yields and high levels of diastereocontrol—poly(hetero)cyclic compounds that would be difficult to access by established methods. Encouraging preliminary results for the enantioselective carboamination of 2,3-dihydrofurans are also disclosed.