Abstract:
We have shown that the conducting polymer PEDOT can mediate Ritter reactions between activated alcohols and nitriles. In addition, PEDOT has been shown to mediate Friedel-Crafts alkylations with stoichiometric amounts of the aromatic substituent in addition to mediating enol alkylations. Although the mechanism of PEDOT remains unclear, the work reported supports the premise that PEDOT is behaving as an alcohol-selective Lewis acid. In addition, the absence of reactivity with styrene along with the results of the tetrahydropyranylation suggest that PEDOT-mediated reactions are not being mediated by putative amounts of triflic acid bound to the polymer or generated in situ. The hypothesis that PEDOT behaves as a Lewis acid is further supported by the slow reaction time seen in the reaction with adamantanol and in the seeming lack of reactivity with triphenylmethanol, both of which could be the result of a steric effect.
