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Synthesis 2009(4): 609-619  
DOI: 10.1055/s-0028-1083352
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of anti-2,7-Disubstituted Norbornadienes

Gavin C. Tsui, Paul Le Marquand, Anna Allen, 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 6 August 2008
Publication Date:
02 February 2009 (online)

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Abstract

Synthesis of a variety of anti-2,7-disubstituted norbornadienes was achieved by palladium- and iron-catalyzed cross-coupling­ reactions of the anti-tert-butoxynorbornadien-2-yl triflate. While the palladium-catalyzed coupling reactions could only generate coupling products with aryl and alkynyl groups, the iron-catalyzed coupling reactions have a much broader scope and provide efficient synthesis of anti-2,7-disubstituted norbornadienes with attached primary, secondary and tertiary alkyl groups, cycloalkyl groups with various ring sizes, as well as vinyl, aryl and alkynyl groups.

Key words

bicyclic compounds - cross-coupling - catalysis - palladium - iron

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