Non-catalytic conversion of C–F bonds of benzotrifluorides to C–C bonds using organoaluminium reagents

J Terao, M Nakamura, N Kambe

Index: Terao, Jun; Nakamura, Misaki; Kambe, Nobuaki Chemical Communications, 2009 , # 40 p. 6011 - 6013

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Citation Number: 18

Abstract

When benzotrifluoride (0.2 mmol) was reacted with trimethylaluminium (1.0 mmol) in a hexane solution at 25 °C for 150 h, t-butylbenzene was obtained in only a 5% yield (Table 1, entry 1). The addition of a chlorinated solvent such as CH 2 Cl 2 or ClCH 2 CH 2 Cl improved the yield of the products obtained from this reaction; the yield was directly proportional to the ε value of the co-solvent (entries 2–5); coordinating solvents (Et 2 O and THF) retarded the reaction ...