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Synthesis 2015; 47(03): 359-366
DOI: 10.1055/s-0034-1378919
DOI: 10.1055/s-0034-1378919
paper
Aryltriolborates as Air- and Water-Stable Bases for Wittig Olefination
Further Information
Publication History
Received: 02 July 2014
Accepted after revision: 10 October 2014
Publication Date:
12 November 2014 (online)
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 compoundsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378919.
- Supporting Information
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