Synthesis of substituted naphthalenes via a catalytic ring-expansion rearrangement.

Adam C Glass, Benjamin B Morris, Lev N Zakharov, Shih-Yuan Liu

Index: Org. Lett. 10(21) , 4855-7, (2008)

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Abstract

A new methodology for the preparation of substituted naphthalenes starting from readily available indenones, organometal reagents, and trimethylsilyldiazomethane via a catalytic rearrangement process is described. Hindered biaryl naphthalenes, including triortho-substituted biaryls, can be accessed through our method. Our results are consistent with a mechanism involving a benzobenzvalene intermediate.