Synthesis 2002(12): 1675-1682
DOI: 10.1055/s-2002-33651
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Sonogashira Coupling of 2,3-Dibromonorbornadiene: Synthesis of Symmetrical and Unsymmetrical Norbornadiene-2,3-diynes

Geoffrey K. Tranmer, William Tam*
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1
Fax: +1(519)7661499; e-Mail: wtam@uoguelph.ca;
Further Information

Publication History

Received 23 April 2002
Publication Date:
05 September 2002 (online)

Abstract

Efficient syntheses of symmetrical (2 steps) and unsymmetrical (3 steps) norbornadiene-2,3-diynes 1 and 2 have been developed. Palladium-catalyzed Sonogashira coupling of 2,3-dibromonorbornadiene (8) with alkynes, using catalytic amount of Pd(PPh3)4, CuI, Et3N or BuNH2 in THF or toluene, provided symmetrical and unsymmetrical norbornadiene-2,3-diynes in good yields.

13

For examples on the study of the effect of solvent in Sonogashira coupling, see Ref. [11c] and references cited therein.

14

See Ref. [11c] and references cited therein.