New Cobalt-Catalyzed Cross-Couplings and Electrophilic Aminations using Organozinc Reagents

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The elaboration of new cobalt-catalyzed cross-couplings involving the formation of new carbon-carbon bonds between mainly Csp³-Csp³ centers will be developed using polyfunctional organic halides and organozinc reagents. The performance of diastereoselective and enantioselective cross-couplings will be emphasized. Applications in the synthesis of natural products such as (-)-munduserone will be done to demonstrate the utility of this new methodology. Also, a new cobalt-catalyzed acylation method using organozinc pivalates and 2-pyridyl thioesters will be studied. Finally, a new cobalt-catalyzed electrophilic amination involving the reaction of organozinc pivalates and halides with hydroxylamine benzoates will be developed. In this topic, it will be important to provide convenient and high yielding preparations of hydroxylamine benzoates. Due to the cheap and low toxic nature of cobalt (compared for example to palladium) the cross-coupling reactions and aminations described in this project have practical relevance and should become helpful tools for the synthetic organic community in the academic and industrial world.