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Synthesis 2011(5): 731-738  
DOI: 10.1055/s-0030-1259484
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Substituted Furans by Iron- and Palladium-Catalyzed Coupling Reactions

Jamie Haner, Kelsey Jack, Jaipal Nagireddy, Mohammed Abdul Raheem, Robin Durham, William Tam*
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada
Fax: +1(519)8244120 (ext. 52268); e-Mail: wtam@uoguelph.ca;
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Publication History

Received 1 October 2010
Publication Date:
31 January 2011 (online)

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Abstract

The synthesis of 2-substituted furans via palladium- and iron-catalyzed coupling utilizing 2-bromofuran is described. Whereas palladium-catalyzed Suzuki coupling effectively provided the corresponding aryl furans, little or no product was obtained by palladium-catalyzed coupling with various alkyl nucleophiles. Iron-catalyzed coupling proved effective for the synthesis of primary and secondary alkyl furans in modest yields and aryl furans in low yields.

Key words

furan - cross-coupling - catalysis - palladium - iron

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