Transition metal-catalyzed cross-coupling reactions have revolutionized organic synthesis, particularly the construction of bonds to sp<sup>2</sup>-hybridized carbons. However, the discovery of analogous reactions of C(sp<sup>3</sup>) electrophiles have lagged behind, despite their potential to deliver a range of important targets, including chiral molecules in high enantiopurity. Towards solving this challenge in organic synthesis, we have developed a range of nickel-catalyzed cross-couplings of alkyl amine and alkyl alcohol derivatives. We have developed stereospecific, nickel-catalyzed cross couplings of benzylic and allylic ammonium salts and carboxylates. These reactions utilize starting materials that are readily available in high optical purity; proceed with high levels of stereochemical fidelity; employ air-stable, functional group tolerance coupling partners, such as aryl boronic acids; and display excellent functional group tolerance. In addition, our cross-couplings of tertiary carboxylates demonstrate that these methods can be used to generate challenging all-carbon, quaternary stereocenters. The optimization, scope, and mechanistic studies of these reactions will be presented.

Stereospecific, nickel-catalyzed cross-couplings

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

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