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Synthesis 2007(8): 1121-1150
DOI: 10.1055/s-2007-966002
DOI: 10.1055/s-2007-966002
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Catalytic Hydration of Alkynes and Its Application in Synthesis
Lukas Hintermann*, Aurélie LabonneInstitut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092391; e-Mail: lukas.hintermann@oc.rwth-aachen.de;
Further Information
Publication History
Received
31 January 2007
Publication Date:
23 March 2007 (online)
Abstract
The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity.
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1 Introduction
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2 Timeline
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3 Alkyne Hydration Catalysts
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3.1 Brønsted Acid and Base Catalysts
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3.2 Mercury Catalysts
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3.3 Non-Mercurial Catalysts for Alkyne Hydration
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3.4 Anti-Markovnikov Hydration of Terminal Alkynes
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3.5 Enzymatic Hydration of Alkynes
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4 Mechanisms of Catalytic Alkyne Hydration
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4.1 Brønsted Acid Catalyzed Hydration
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4.2 Mercury-Catalyzed Hydration
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4.3 Other-Metal-Catalyzed Markovnikov Hydrations
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4.4 Mechanism of Ruthenium-Catalyzed Anti-Markovnikov Hydration
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5 Substrate Spectrum and Selectivity of Catalytic Alkyne Hydration
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5.1 Markovnikov Hydration Catalysis
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5.2 Anti-Markovnikov Hydration Catalysts
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6 Reactions Related to Catalytic Alkyne Hydration
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7 Conclusions and Outlook
Key words
alkynes - catalysis - hydration - ketones - aldehydes
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References
Thermodynamic values calculated with data from:
http://webbook.nist.gov/chemistry/ (accessed January 2007). Note that phase-changes will affect ΔrG/ΔrH.
See section 3.3.5 for a Cu-catalyst that generates considerable amounts of anti-Markovnikov product.
141dppe = 1,2-bis(diphenylphosphino)ethane; dppb = 1,4-bis(diphenylphosphino)butane.
142Py-BOX- i Pr = 2,6-bis(4-(isopropyl)-2-oxazolin-2-yl)pyridine.
147Note that Grotjahn’s complex D is available in research quantities from Strem Chemicals.
150Hintermann, L.; Labonne, A.; Kribber, T.; Paciok, E. unpublished results.
154Kribber, T.; Labonne, A.; Hintermann, L. manuscript submitted.
155Bolm, C.; Labonne, A.; Zani, L.; Hintermann, L. manuscript in preparation.
274The price of 1 g of AuMe(PPh3) corresponds to that of 1 kg of mercury(II) sulfate!