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Triethylsilyl Perfluoro-Tetraphenylborate, [Et 3 Si + ][F 20 -BPh 4 – ], a Widely Used Nonexistent Compound

2011; American Chemical Society; Volume: 30; Issue: 17 Linguagem: Inglês

10.1021/om200636u

1520-6041

Matthew Nava, Christopher A. Reed,

Fluorine in Organic Chemistry

The commonly used triethylsilyl perfluoro-tetraphenylborate salt, [Et3Si+][F20-BPh4–], has been misidentified. As prepared, the cation is a hydride-bridged silane adduct [R3Si–H–SiR3+]. Under favorable circumstances it can be an effective source of the triethylsilylium ion Et3Si+, but in the absence of a stabilizing base the potent electrophilicity of Et3Si+ decomposes the "inert" F20-BPh4– counterion.