Novel route to 2-substituted benzo[b]thiophenes using functionalised titanium alkylidene reagents

ORGN 388

Christine F. Roberts and Richard C. Hartley. Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, United Kingdom
Benzo[b]thiophenes are of great current interest due to their many useful biological properties. There are many benzo[b]thiophene derivatives currently in pharmaceutical use or development.

Novel solid-supported functionalised titanium alkylidene reagents, containing a TBS protected sulfur nucleophile ortho to the alkylidene, have been employed to synthesise 2-substituted benzo[b]thiophenes in good yield and excellent purity, with no trace of the site of attachment to the solid-support. Merrifield resin is used and no special linker is required.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003