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Gold- and Silver-Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives

Pennell, MN; Turner, PG; Sheppard, TD; (2012) Gold- and Silver-Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives. Chemistry - A European Journal , 18 (15) 4748 - 4758. 10.1002/chem.201102830. Green open access

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Abstract

A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer–Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.

Type:Article
Title:Gold- and Silver-Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives
Open access status:An open access version is available from UCL Discovery
DOI:10.1002/chem.201102830
Publisher version:http://dx.doi.org/10.1002/chem.201102830
Language:English
Additional information:This is the peer reviewed version of the following article: Pennell, MN; Turner, PG; Sheppard, TD; (2012) Gold- and Silver-Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives. Chemistry - A European Journal , 18 (15) 4748 - 4758. , which has been published in final form at 10.1002/chem.201102830. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving PubMed ID: 22374879
Keywords:gold, homogeneous catalysis, Meyer-Schuster rearrangement, propargylic alcohols, silver
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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