Alkylation of the K-Region in a Sterically Hindered Pyrene Carboxamide via Directed Reaction with Alkyllithiums under Air

Sterically hindered N,2,7-tri-tert-butylpyrene-1-carboxamide treated with n-BuLi, i-BuLi, s-BuLi, and n-HexLi in THF in the presence of TMEDA and air afforded trans-N,2,7-tri-tert-butylpyrene-10-alkyl-9-hydroxy-9,10-dihydropyrene-1-carboxamides in 63–74% yield. Trifluoroacetic acid promoted dehydration of these compounds gave 10-alkyl derivatives of the starting amide in 79–89% yield. The minor products of this reaction were deamidated compounds, 4-alkyl-2,7-di-tert-butylpyrenes.