Summer Baker Dockrey
Mentor: Jason Schmink
The palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. For decades, 1,3-dithianes have been used as nucleophiles with aldehydes, ketones and primary and secondary alkyl halides, but have yet to be used as nucleophilic transmetalation reagents. The acidity of 2-aryl-1,3-dithianes is exploited and used for the first time as a transmetalation reagent in a palladium cross-coupling reaction. Cross-coupling of a range of aryl and alkyl dithianes with aryl and heteroaryl halides including scope and limitations is presented. Stream-lined utility of the umpolung transmetalating reagent also affords divergent deprotection to a) the diaryl methane by Raney Nickel or b) oxidation to the ketone.