Bismuth(III) triflate is an efficient catalyst for Friedel-Crafts cyclizations of tertiary alcohols to form 1,1-disubstituted fused-ring tetrahydro aromatic and heteroaromatic systems. This versatile catalyst permits the synthesis of a variety of core structures found in drug compounds, including tetrahydronaphthalenes, tetrahydroquinolines, tetrahydroisoquinolines, chromans and thiochromans. The isolated yields range from 80-97% and products are afforded with a minimum of substrate fragmentation, which was a problem in earlier reactions catalyzed by Amberlyst-15� and aluminum chloride. The functional group tolerance of the catalyst allows the cyclization of numerous substrates and even promotes cyclization with deactivated aromatic rings.

Bismuth(III) triflate as an efficient catalyst for cyclizations to form 1,1-disubstituted tetrahydro aromatic and heteroaromatic systems

245th National Meeting (2013)

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