Publication Details (including relevant citation information):
Dmitri Gelman, Dmitry Tsvelikhovsky, Gary A. Molander, and Jochanan Blum
J. Org. Chem., 2002, 67 (18), pp 6287–6290
Publication Date (Web): August 15, 2002 (Article)
Department of Organic Chemistry, The Hebrew University, Jerusalem 91904, Israel, and Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
Sodium tetraalkynylaluminates, prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both ****- and heterocyclic aryl bromides and can be used for conversion of polybromo compounds into polyalkynes. The reactions are high yielding and selective, free of undesired homocoupling and hydrogenolysis processes. The reagents selectively react with the ring-bound bromine atoms but do not affect chloro, cyano, triflate, or ester functions.
Address (URL): http://pubs.acs.org/doi/pdf/10.1021/jo020169q