Synthesis of (E)-(2-Arylethenyl)silanes by Palladium-Catalyzed Arylation of Vinylsilanes in the Presence of Silver Nitrate

Article abstract of DOI:10.1021/jo00376a044

A series of (E)-trimethyl(2-arylethenyl)silanes 1-16 and (E)-triethoxy(2-arylethenyl)silanes 17 and 18 has been synthesized by palladium-catalyzed arylation of the corresponding vinylsilanes, in the presence of silver nitrate.Apart from enhancing the rate of the reaction, silver nitrate also completely suppresses the desilylation.In the absence of silver salt, under ordinary Heck arylation conditions, styrene derivatives are formed in good yields.A possible mechanistic rationale for the formation of styrenes is discussed.