P(C1C=CC=CC=1)(C)C.FC(F)(F)S(O[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]=1[Cl:26])(=O)=O.[C:29](#[N:32])[CH:30]=[CH2:31].C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C>[Cl:26][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1/[CH:31]=[CH:30]/[C:29]#[N:32]
Pd(OAc)2 (3 mol %, 11 mg), PMe2Ph (5 mol %, 11 mg), 1-chloronaphthalen-2-yl trifluoromethanesulfonate (500 mg, 1.61 mmol), acrylonitrile (103 mg, 1.93 mmoli), triethylamine (242 mg, 2.4 mmol) and 15 mL of acetonitrile were added to a microvawe vial and the mixture was irradiated by MW at 120° C. for 1 h. At the conclusion of the reaction, the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane and washed with water; the organic layer was filtered through a pad of silica gel with copious washings, concentrated, and purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate (93:7) to give (2E)-3-(1-chloronaphthalen-2-yl)prop-2-enenitrile as colourless oil (120 mg, 35% yield).
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