Aryltriolborates as Air- and Water-Stable Bases for Wittig Olefination

Abstract

Tetrabutylammonium aryltriolborates have been synthesized in 37–66% yield by a one-pot procedure from arylboronic acids, 1,1,1-tris(hydroxymethyl)ethane, and aqueous tetrabutylammonium hydroxide. The aryltriolborates can be used as bases in Wittig reactions of aromatic aldehydes with all three types of phosphorus ylides: stabilized and semistabilized ylides can be generated at room temperature, and nonstabilized ylides at 120 °C (bath temperature).

Key words

tetrabutylammonium aryltriolborates - Wittig olefination - phosphorus ylides - organic bases - organoboron compounds

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