Greetings! I bring you the good news that our paper describing the synthesis of styrenes from two aldehyde starting materials has been published by The Journal of Organic Chemistry (Here’s a link). This work began with a chance observation that Grant Dixon made when studying a TMSOTf-promoted aldehyde-aldehyde aldol reaction; I was willing to let it go but Grant insisted on following up, and it’s become one of our most significant contributions to the literature in the history of the Downey Group. Michael Rodriguez greatly expanded the scope of the reaction and found ways to make some of the more recalcitrant substrates react. Kevin Kim nailed down the importance of the aldehyde group in the eventual styrene generation step, and Tyler Chong elucidated the key carbocation-formation step for the mechanism, as well as dealt with some interesting reviewer comments after we submitted the initial draft.
Congratulations to all these great students on completing a project the pandemic couldn’t stop.
Dixon, Grant J.; Rodriguez, Michael R.; Chong, Tyler G.; Kim, Kevin Y.; Downey, C. Wade “Synthesis of b,b-Disubstituted Styrenes via Trimethylsilyl Triflouromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination” J. Org. Chem. 2022, 87, 14846-14854.