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A consecutive sequential two stage synthetic strategy for the preparation of eleven novel 1-trimethylsilyl-2arylcyclopentenes is reported. In the first stage, the Suzuki reaction of 1-bromo-2-chlorocyclopentene with eleven arylboronic acids in aqueous conditions yielded the novel 1-chloro-2-arylcyclopentenes in 91-96% yields. The single crystal XRD structures of two representative 1-chloro-2-arylcyclopentenes are highlighted. In the second stage, the Wurtz–Fittig coupling reaction of the 1-chloro-2-arylcyclopentenes with metallic sodium and chlorotrimethylsilane in anhydrous ether afforded the anionic synthons: 1-trimethylsilyl-2arylcyclopentenes in 62-82% yields. A library of twenty-two novel compounds from the two stages is reported. Pd(OAc)2 Na2CO3, TBAB H2O, 80° C Ar, MW Na, TMS-Cl

A highly efficient synthesis of 1-trimethylsilyl-2-arylcyclopentenes using two consecutive stages of aqueous and anhydrous reactions