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Synlett 2012(6): 897-902  
DOI: 10.1055/s-0031-1290619
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Cationic Gold-Catalyzed Regioselective Hydration of 1-Arylalkynes through Carbonyl Group Participation

Jiseon Jeong, Devalina Ray, Chang Ho Oh*
Department of Chemistry, Hanyang University, Sungdong-Gu, Seoul 133-791, Korea
Fax: +82(2)22990762; e-Mail: changho@hanyang.ac.kr;
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Publication History

Received 19 November 2011
Publication Date:
15 March 2012 (online)

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Abstract

The unsymmetrically substituted internal alkynes were regioselectively hydrated through carbonyl-group participation using cationic gold catalyst where the nature and position of carbonyl functionalities play a key role in governing the regioselectivity of products as well as facilitating the reaction. A new atom-economical, cationic gold-catalyzed regioselective hydration of 1-aryl­alkynes substituted with various functionalities in the absence of any toxic catalyst, strong acid, or other additives have been reported.

Key words

catalysis - regioselectivity - internal alkynes - hydration

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