Great news for all you Downey Group fans out there: We have a new paper out in The Journal of Organic Chemistry. The reaction that Eric Zhou worked on for two and a half years, the silyloxyalkylation of 3-alkylated indoles, is now free for the world to view at this link. Based on some insightful early work from Helen Xia ’24, Eric found that if you subject indoles that have already been alkylated at the more nucleophilic C3 position to aldehydes in the presence of TMSOTf and lutidine, silyloxyalkylation can occur. Workup with TBAF provides an alcohol that would otherwise be prohibitively expensive to make. Nobody else in the world can do this reaction without it decomposing into other side products. Congratulations to Helen and Eric!
Published: Friedel–Crafts Chemistry of Indoles at C2