Synthesis of naphthalenes and 2-naphthols via electrophilic cyclization

ORGN 123

Xiaoxia Zhang, xxzhang@iastate.edu, Sampa Sarkar, and Richard C Larock. Department of Chemistry, Iowa State University, Ames, IA 50011
A wide variety of substituted naphthalenes are readily prepared under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols with ICl, I2, Br2, NBS, and PhSeBr as electrophiles. The analogous cyclization of 1-aryl-3-alkyn-2-ones with ICl and I2 provides a new synthetic method to 3-iodo-2-naphthols. This methodology readily accommodates various functional groups. Iodo-substituted dibenzothiophenes and carbazoles can also be regioselectively achieved when the cyclization is extended to systems containing heterocyclic rings, such as benzothiophenes and indoles.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005