Alkyl amines are inexpensive and widely abundant chemicals in organic synthesis, making them attractive substrates for further functionalization. Functionalization via cleavage of the carbon–nitrogen (C–N) bond has recently been discovered as a powerful transformation of these abundant, easily protected alkyl amines. Due to the prevalence of C(sp<sub>3</sub>)−C(sp<sub>3</sub>) bonds in bioactive molecules, methods to create alkyl-alkyl bonds have become increasingly desirable. By using High-Throughput Experimentation interfaced with traditional reaction optimization, we have developed a nickel-catalyzed cross-coupling of alkyl pyridinium salts with alkyl boron species formed in situ from an alkene. The optimization, scope, and mechanistic understanding of these reactions will be presented.

Deaminative alkyl-alkyl cross-couplings of alkylpyridinium salts and alkenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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