The zincation of various 1-(trimethylsilyl)-3-aryl-1-propynes with TMPZnCl路LiCl followed by a Pd-catalyzed coupling with aryl halides provides arylated allenes in 52鈥?2% yield. Subsequent metalation with TMPZnCl路LiCl and cross-coupling with a second different aryl halide provides regioselectively tetrasubstituted allenes in 42鈥?0% yield. This sequence can be performed in a one-pot procedure. DFT calculations and NMR studies support the formation of allenylzinc and propargyllithium intermediates starting from 1-(trimethylsilyl)-3-phenyl-1-propyne.