Synthesis of substituted naphthalenes via a catalytic ring-expansion rearrangement.
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.
Department of Chemistry, University of Oregon, Eugene, Oregon 97403, USA.
Adam C
AC
Glass
Benjamin B
BB
Morris
Lev N
LN
Zakharov
Shih-Yuan
SY
Liu
D002384:Catalysis; D007192:Indenes / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
D007192:Indenes; D009281:Naphthalenes; C093581:indene