Scope of arene perfluroalkylation using iron reagents

CHED 1220

Samuel D Timpa, stimpa@centenary.edu, Matthew P. Clark, mclark@centenary.edu, Bryon W. Larson, bwlarson@centenary.edu, and Joshua D. Lawrence, jlawrenc@centenary.edu. Department of Chemistry, Centenary College of Louisiana, 2911 Centenary Blvd., Shreveport, LA 71104
Substrate scope for the perfluoroalkylation of arenes using FeI(C4F9)(CO)4 or [Fe(μ-I)(C4F9)(CO)3]2 in conjunction with AgO2CCF3 will be described. We found the substrate scope to depend largely on the electron density of the substituents. The yields for arenes with electron-donating groups were greater than those with electron-withdrawing groups. This trend continued with disubstituted arenes. Site selectivity also varied with the monosubstituted arenes. Competition reactions were also performed between benzene and substituted arenes. The arenes with electron donating substituents were preferred over benzene, while benzene was preferred over arenes with electron withdrawing substituents. Thiophene and furan were also amenable to perfluoroalkylation, giving primarily the 2-perfluorobutyl product.
 

Undergraduate Research Poster Session: Inorganic Chemistry
2:00 PM-4:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008