On-Surface Heck Reaction of Aryl Bromides with Alkene on Au(111) with Palladium as Catalyst
Ke-Ji Shi1, Chen-Hui Shu1, Cheng-Xin Wang1
1Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, State Key Laboratory of Chemical Engineering and School of Chemistry & Molecular Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
Abstract:
The on-surface Heck reaction of aryl bromides with terminal alkene has been achieved for the first time. With palladium as the catalyst, cross-coupling of porphyrin-derived aryl bromides with terminal alkene proceeds with high selectivity on an Au(111) surface, as determined by scanning tunneling microscopy at the single molecular level. Density functional theory calculations suggest that the on-surface Heck reaction proceeds via debromination of aryl bromide, addition to the C═C bond, and elimination of hydrogen, ultimately affording the cross-coupling product.
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