2-Azaallyl Anions and Sulfenate Anions: Unusual and Unexpected Reactivity
Professor Patrick J. Walsh (University of Pennsylvania, Department of Chemistry)
Host: Professor Qiu Wang
Tuesday, November 14, 2017 - 11:40am to 1:10pm
Location: French Family Science Center 2237
Rosenthal, Janet

Link for Professor Walsh

Abstract:  The umpolung synthesis of diarylmethylamines via palladium-catalyzed arylation of 2-azaallyl anion intermediates and related reactions will be presented. Next, the observation that that 2-azaallyl anions can behave as organic super-electron-donors (SED) will be introduced. Such unique behavior is illustrated in (i) generation of 2-azaallyl radicals from single-electron-transfer (SET) between 2-azaallyl anions and neutral ketimines, which then couple with vinyl bromides; (ii) generation of 2-azaallyl radicals from SET of 2-azaallyl anions with aryl and alkyl electrophiles, which generate aryl and alkyl radicals leading to formation of C–C bonds. Finally, some novel organocatalysts will be described.