Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins:  Use of a Strong Nucleophile to Generate a Strong Base

Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins:  Use of a Strong Nucleophile to Generate a Strong Base

The direct addition of water and a variety of alcohols to activated olefins was observed in the presence of nucleophilic phosphine catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals, or strong acids or bases. The use of simple commer...

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Veröffentlicht in:Journal of the American Chemical Society 2003-07, Vol.125 (29), p.8696-8697
Hauptverfasser: Stewart, Ian C, Bergman, Robert G, Toste, F. Dean
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Organic chemistry
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container_issue 29
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container_title Journal of the American Chemical Society
container_volume 125
creator Stewart, Ian C
Bergman, Robert G
Toste, F. Dean
description The direct addition of water and a variety of alcohols to activated olefins was observed in the presence of nucleophilic phosphine catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals, or strong acids or bases. The use of simple commercially available catalysts makes this an attractive method for the preparation of β-hydroxy and β-alkoxy substrates, which are prevalent targets and intermediates in organic synthesis. The scope and mechanism of this reaction has been explored, and the compound that acts as the resting state of the catalyst was synthesized independently. Our mechanism also suggests the possibility of extending the scope of this reactivity to other classes of nucleophiles.
doi_str_mv 10.1021/ja035232n
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Organic chemistry
title Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins:  Use of a Strong Nucleophile to Generate a Strong Base
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