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8.3.7.9 Method 9: Metalation of Alkylarenes with Superbases

DOI: 10.1055/sos-SD-008-01267

Mordini, A.; Valacchi, M.Science of Synthesis, (200681459.

When alkylbenzene derivatives are submitted to metalation, the metal may effect deprotonation either at a benzylic or a ring hydrogen site (preferably at the sterically unhindered meta or para positions). To avoid contamination by the ring-metalated derivative, α-deprotonation of toluene requires a mixture of butyllithium/potassium tert-butoxide (LICKOR).[‌12‌,‌194‌,‌195‌] Use of, N,N,N,N-tetramethylethylenediamine-activated butyllithium, for example, gives rise to some contamination by ring-metalated products.[‌196‌,‌197‌] Examples of mono- and dimetalated alkylbenzenes are given in Table 6.

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References


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