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On-Surface Synthesis of a Five-Membered Carbon Ring from a Terminal Alkynyl Bromide: A [4 + 1] Annulation
Tao Wang1,2,3, Yu Pan4,5, Wenzhao Zhang1
1National Synchrotron Radiation Laboratory, Department of Chemical Physics and Key Laboratory of Surface and Interface Chemistry and Energy Catalysis of Anhui Higher Education Institutes, University of Science and Technology of China, Hefei 230029, P.R. China.
Abstract:
We report an on-surface synthesis of five-membered carbon ring via a [4 + 1] annulation reaction, starting from a simple terminal alkynyl bromide, 4-(bromoethynyl)biphenyl, on Ag(110). The combination of scanning tunneling microscopy (STM), synchrotron radiation photoemission spectroscopy (SRPES), and density functional theory (DFT) calculations unravel the reaction pathway and mechanism. Three basic reaction steps are involved, successively including the formation of alkynyl-Ag-alkynyl bridged organometallic dimer, the generation of alkylidene carbene intermediate, and the final [4 + 1] annulation involving a hydrogen transfer step.
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