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Synthesis 2011(13): 2101-2116  
DOI: 10.1055/s-0030-1260054
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Site-Selective Suzuki-Miyaura Reactions of 1,4- and 3,5-Bis(trifluoromethylsulfonyloxy)-2-naphthoates

Muhammad Farooq Ibada, Nadi Eleyaa, Abid Obaid-Ur-Rahmana, Ahmed Mahala, Munawar Hussaina, Alexander Villingera, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
b Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
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Publication History

Received 12 December 2010
Publication Date:
19 May 2011 (online)

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Abstract

The Suzuki-Miyaura reaction of phenyl 1,4-bis(trifluoro­methylsulfonyloxy)-2-naphthoate and ethyl 3,5-bis(trifluoromethylsulfonyloxy)-2-naphthoate afforded various 1,4- and 3,5-diaryl-2-naphthoates with very good site-selectivity, respectively. The first attack occurred at the sterically more hindered positions C-1 and C-3, respectively. The selectivity can be explained by the electronic influence of the ester group.

Key words

catalysis - palladium - Suzuki-Miyaura reaction - site-selectivity - naphthalene derivatives

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