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Review
. 2016 Nov 30:12:2577-2587.
doi: 10.3762/bjoc.12.253. eCollection 2016.

Catalytic Wittig and aza-Wittig reactions

Zhiqi Lao  1 , Patrick H Toy  1
Affiliations
Review

Catalytic Wittig and aza-Wittig reactions

Zhiqi Lao et al. Beilstein J Org Chem. .

Abstract

This review surveys the literature regarding the development of catalytic versions of the Wittig and aza-Wittig reactions. The first section summarizes how arsenic and tellurium-based catalytic Wittig-type reaction systems were developed first due to the relatively easy reduction of the oxides involved. This is followed by a presentation of the current state of the art regarding phosphine-catalyzed Wittig reactions. The second section covers the field of related catalytic aza-Wittig reactions that are catalyzed by both phosphine oxides and phosphines.

Keywords: Wittig reactions; aza-Wittig reactions; catalysis; phosphine oxides; phosphines; reduction; silanes.

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Figures

Scheme 1
Scheme 1
Prototypical Wittig reaction involving in situ phosphonium salt and phosphonium ylide formation.
Scheme 2
Scheme 2
Bu3As-catalyzed Wittig-type reactions.
Scheme 3
Scheme 3
Ph3As-catalyzed Wittig-type reactions using Fe(TCP)Cl and ethyl diazoacetate for arsonium ylide generation.
Figure 1
Figure 1
Recyclable polymer-supported arsine for catalytic Wittig-type reactions.
Scheme 4
Scheme 4
Bu2Te-catalyzed Wittig-type reactions.
Scheme 5
Scheme 5
Polymer-supported telluride catalyst cycling.
Scheme 6
Scheme 6
Stable and odourless telluronium salt pre-catalyst for Wittig-type reactions.
Scheme 7
Scheme 7
Phosphine-catalyzed Wittig reactions.
Figure 2
Figure 2
Various phosphine oxides used as pre-catalysts.
Scheme 8
Scheme 8
Enantioselective catalytic Wittig reaction reported by Werner.
Scheme 9
Scheme 9
Base-free catalytic Wittig reactions reported by Werner.
Scheme 10
Scheme 10
Catalytic Wittig reactions reported by Lin.
Scheme 11
Scheme 11
Catalytic Wittig reactions reported by Plietker.
Scheme 12
Scheme 12
Prototypical aza-Wittig reaction involving in situ iminophosphorane formation.
Scheme 13
Scheme 13
First catalytic aza-Wittig reaction reported by Campbell.
Scheme 14
Scheme 14
Intramolecular catalytic aza-Wittig reactions reported by Marsden.
Scheme 15
Scheme 15
Catalytic aza-Wittig reactions in 1,4-benzodiazepin-5-one synthesis.
Scheme 16
Scheme 16
Catalytic aza-Wittig reactions in benzimidazole synthesis.
Scheme 17
Scheme 17
Phosphine-catalyzed Staudinger and aza-Wittig reactions.
Scheme 18
Scheme 18
Catalytic aza-Wittig reactions in 4(3H)-quinazolinone synthesis.
Scheme 19
Scheme 19
Catalytic aza-Wittig reactions of in situ generated carboxylic acid anhydrides.
Scheme 20
Scheme 20
Phosphine-catalyzed diaza-Wittig reactions.
See this image and copyright information in PMC

References

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