Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, α,α-disubstituted aldehydes condense with electron-rich aromatic aldehydes to yield β, β- disubstituted styrenes. More electron-rich aromatic aldehydes react more rapidly and in higher yield. Preliminary results suggest that the reaction may proceed via the ionization and formal deformylation of an aldol intermediate.
Document Type
Article
Publication Date
2022
Publisher Statement
Copyright © 2022, The Journal of Organic Chemistry.
Recommended Citation
Grant J. Dixon, Michael R. Rodriguez, Tyler G. Chong, Kevin Y. Kim, C. Wade Downey. Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Addition-Deformylative Elimination. The Journal of Organic Chemistry 2022, 87, 14846-14854.