The palladium-catalyzed cross-coupling of aryl electrophiles with substituted Corey-Seebach <i>umpolung</i> reagents is described. For decades, the anions of 1,3-dithianes have been used as polarity-reversed nucleophiles, reacting with, for example, aldehydes, ketones, and primary and secondary alkyl halides. Recently, we disclosed the first examples using 1,3-dithianes as transmetalation reagents. To date we have used this new strategy to synthesize medically relevant motifs, including diaryl ketones and diarylmethanes. Throughout our investigations, we have unearthed some unexpected, mechanistically interesting variations on our initial findings when employing various surrogates for 1,3-dithianes. The expanding reaction scope, our group's current mechanistic understanding, and the current future goals are presented.

Development of Corey-Seebach <i>umpolung</i> reagents in palladium-catalyzed cross-coupling reactions

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Development of Corey-Seebach umpolung reagents in palladium-catalyzed cross-coupling reactions