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Redox-neutral organocatalytic Mitsunobu reactions

Authors: Beddoe, Rhydian; Andrews, Keith; Magné, Valentin; Cuthbertson, James; Saska, Jan; Shannon-Little, Andrew; Shanahan, Stephen; +2 Authors

Redox-neutral organocatalytic Mitsunobu reactions

Abstract

Displacing OH groups catalytically The Mitsunobu reaction is widely used to invert the configuration of alcohols. However, its major drawback is the need to activate the alcohol with a full equivalent of phosphine, thereby generating a phosphine oxide co-product. Beddoe et al. report a phosphine oxide compound that achieves the same result catalytically (see the Perspective by Longwitz and Werner). The key is a phenol substituent that can reversibly bond through its oxygen to phosphorus, forming a ring that the alcohol opens. The phosphorus thus remains in the +5 oxidation state throughout the reaction, and water is the only by-product. Science , this issue p. 910 ; see also p. 866

Keywords

[CHIM] Chemical Sciences

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    popularity
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    influence
    This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
189
Top 1%
Top 10%
Top 1%
hybrid