Emmert, Marion H
alpha-aminonitriles are intermediates for synthesis of alpha-functionalized amines. Protocols for accessing alpha-aminonitriles largely use alkyl halides, which are toxic and generate stoichiometric amounts of halogenated waste upon transformation. Thus the development of a one pot synthesis for alpha-aminonitriles from amines is important to study. Our research on iron-catalyzed tertiary amine oxidation is thought to proceed through an iminium intermediate, described in current alpha- cyanation protocols of tertiary amines. Thus we employed cyanide as a nucleophile for alpha- cyanations, resulting in the generation of the corresponding alpha-aminonitriles. Indolation and trifluoromethylation reactions were explored during the development of the alpha-cyanation protocol.
Worcester Polytechnic Institute
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Chemistry and Biochemistry
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