Tetrahedron letters

Lanthanide assisted cross-coupling of aryl bromides with triethylaluminum

M Shenglof, D Gelman, GA Molander, J Blum

Index: Shenglof, Margarita; Gelman, Dmitri; Molander, Gary A.; Blum, Jochanan Tetrahedron Letters, 2003 , vol. 44, # 47 p. 8593 - 8595

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Citation Number: 18

Abstract

Interaction of equimolar quantities of 1-bromonaphthalene and triethylaluminum in the presence of 5 mol% of PdCl 2 (PPh 3 ) 2 in THF at 22°C afforded after 6 h 16% of 1-ethylnaphthalene and 5% of naphthalene. Upon addition of an equimolar amount of dry CeCl 3 , the yield of 1-ethylnaphthalene increased to 88% and that of the dehalogenated naphthalene decreased to 0.6%. (The remaining 11% was the unreacted aryl bromide.) When the time was extended to 10 h full ...