American Chemical Society
ol0c03144_si_001.pdf (3.22 MB)

Relay Palladium/Copper Catalysis Enabled Silylative [5 + 1] Benzannulation Using Terminal Alkynes as One-Carbon Units

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journal contribution
posted on 2020-10-19, 22:07 authored by Li-Jun Wu, Fan Teng, Gui-Fen Lv, Jin-Heng Li
Using terminal alkyne as a nontraditional one-carbon (C1) unit and silylborane as an external silicon pronucleophile, a relay palladium/copper-catalyzed silylative [5 + 1] benzannulation of 3-acetoxy-1,4-enynes for producing polysubstituted arylsilanes, especially including bioactive motif-based analogues, in a single reaction step through benzene ring skeleton assembly and silyl intermolecular incorporation cascades is developed. Mechanistic studies show that this reaction allows the terminal sp-hybridized carbon atom in terminal alkynes as a C1 unit via cleavage of two π-bonds and one C­(sp)–H bond.