Neighboring carbonyl group assisted hydration of unsymmetrical aryl alkynes overriding regular selectivity

Mendhekar, Kishor L., Pradhan, Tapas R., Mallampudi, N. Arjunreddy and Mohapatra, Debendra K. 2019. Neighboring carbonyl group assisted hydration of unsymmetrical aryl alkynes overriding regular selectivity. European Journal of Organic Chemistry 2019 (33) , pp. 5787-5797. 10.1002/ejoc.201900941

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Abstract

A mild and highly regioselective gold-catalyzed hydration of γ-acetoxy aryl alkynes leading to anti-Markovnikov products by the assistance of a neighboring carbonyl group is presented. The reaction procedure operates under room temperature conditions with broad functional group tolerance in presence of more than stoichiometric amount of water to access two different types of acyloins in good to excellent yields. Acetate protected acyloins were produced from primary and secondary substrates, while tertiary ones react differently to give free-acyloins under identical conditions. The mechanistic pathways for such divergent functionalization were deduced from isotopic mechanistic results.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1434-193X
Last Modified:	26 Jan 2024 14:45
URI:	https://orca.cardiff.ac.uk/id/eprint/165579

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