Shvo catalyst at work

05 April 2010 - Catalysis

Bähn et al. have demonstrated a new application of the Shvo catalyst with the N-alkylation of indole by hexanol (DOI) . This reaction is a indirect reductive amination with the alcohol first oxidized to the aldehyde by transfer hydrogenation from the indole which then reacts with the amine to the enamine which isomerizes. By adding a small amount of p-toluenesulfonic acid both conversion and selectivity increases (less C-alkylation). Traditional methods for N-alkylation are messy when they involve alkyl halides.

Another recent alcohol N-alkylation but not catalytic is one based on a Mitsunobu reaction (Bombrun et al. 2002 DOI)