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Pure Appl. Chem., 2013, Vol. 85, No. 6, pp. 1161-1173

Published online 2013-05-10

Gold(I)-catalyzed formation of bridged and fused carbocycles

Francis Barabé, Patrick Levesque, Boubacar Sow, Gabriel Bellavance, Geneviève Bétournay and Louis Barriault*

Center for Catalysis Research and Innovation, Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa K1N 6N5, Canada

Abstract: For many years, despite a rich coordination chemistry, gold (Au) was judged as being catalytically inactive for the formation of carbon–carbon bonds. In mid-1970, few reports demonstrated that Au salts could be very useful reagents to catalyze organic transformations. In recent years, homogeneous catalysis by Au has received considerable attention by the scientific community. It was shown that Au(I) or (III) catalysts are specific and more reactive than most of the other soft Lewis acids such as Hg(II), Cu(II), Pt(II), and Pd(II). Taking advantage of the affinity of cationic phosphine Au complexes to triple bonds, we conceived a Au(I)-catalyzed 6-endo-dig cyclization of cyclic enol ether to prepare bridged and fused bicyclic ketone. Keeping in mind that 5-exo-dig cyclizations can be a competitive process, we surveyed various Au(I) complexes.