The Journal of organic chemistry

A Gallium-Catalyzed Cycloisomerization/Friedel− Crafts Tandem

HJ Li, R Guillot, V Gandon

Index: Li, Hui-Jing; Guillot, Regis; Gandon, Vincent Journal of Organic Chemistry, 2010 ,  vol. 75,  # 24  p. 8435 - 8449

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Citation Number: 44

Abstract

Under noble (Au, Pt, Ru) and group 13 (Ga, In) metals catalysis, 1, 6-arenynes rearrange to give 1, 2-dihydronaphthalenes in a high yielding, regiocontrolled fashion. When the reaction is carried out in the presence of electron-rich arenes (anisole, phenol, indole derivatives), Friedel− Crafts addition may follow the cycloisomerization step. Only GaX3 salts proved able to catalyze these two C− C bond formation events. This specificity of gallium has been ...