Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols

Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperature in dichloromethane). Preliminary mechanist...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 9; pp. 1758 - 1766
Main Authors Georgy, Marie, Boucard, Valérie, Debleds, Olivier, Zotto, Christophe Dal, Campagne, Jean-Marc
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.02.2009
Elsevier
Subjects
Chemical Sciences
Cheminformatics
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
1,5-ENYNES
BOND-FORMING REACTIONS
ISOMERIZATION
ALLYLATION
BENZYLATION
CATALYZED DIRECT AMINATION
ALKYNYLATION
1,3-DICARBONYL DERIVATIVES
CATIONS
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Summary:Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperature in dichloromethane). Preliminary mechanistic investigations suggest a mechanism through a carbocation intermediate. Nucleophilic substitutions on allylic and benzylic alcohols are also described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.12.051