Efficient Cross-Coupling Reactions of (Pivaloyloxymethyl)zinc Chloride

Abstract

(Pivaloyloxymethyl)zinc chloride, obtained by an iodine–magnesium exchange and subsequent transmetalation, shows a much higher reactivity in Negishi cross-couplings than the corresponding zinc organometallic, prepared by direct zinc insertion. Furthermore, a substituted derivative of (pivaloyloxymethyl)zinc chloride is prepared starting from pivaloyloxymethyl sulfoxide using TMPZnCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl), followed by a sulfoxide–magnesium exchange.

Key words

organozinc reagents - carbenoids - cross-coupling - palladium - sulfoxides

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