Alkenes are used in the chemical synthesis of plastics, fine chemicals, and biologically active molecules including medicines. The simplest alkene, ethylene, is an important plant hormone that can be used in agriculture to ripen fruits. The palladium-catalyzed Suzuki cross coupling reaction is an efficient method to synthesize substituted alkenes with control of the 3-dimensional geometry of the groups bonded to the alkene. An alkyl-substituted alkyne was found to undergo a 9-BBN catalyzed hydroboration reaction with pinacolborane to produce the alkyl-substituted, (E)-alkenylboronic acid pinacol ester in 69% yield. The palladium-catalyzed cross-coupling of this alkyl-substituted, (E)-alkenylboronic acid pinacol esters was then studied with aryl chlorides. The reaction parameters were evaluated to maximize the yield of the cross-coupling product. The scope of compatible aryl chlorides was then evaluated under the optimized reaction conditions. Nine ortho- and para-substituted aryl chlorides bearing various electron-donating and electron-withdrawing groups were found to undergo the coupling reaction with the alkyl-substituted, (E)-alkenylboronic acid pinacol ester in 54%-98% yield.