In the past few decades, alcohol derivatives have been developed as novel electrophiles in transition metal-catalyzed cross couplings via C–O bond activation. In particular, exceptional developments in stereospecific cross-couplings have harnessed highly enantioenriched benzylic alcohol-derived substrates. However, one of the widespread limitations in this field is the need for substrates substituted with naphthyl groups or other extended π systems. Additionally, most of these cross-couplings are limited to the formation of tertiary stereocenters. Herein, we report the development of a catalyst system that overcomes these longstanding limitations. Our nickel-catalyzed, mild Suzuki-Miyaura coupling of tertiary esters harnesses readily available enantioenriched benzylic alcohol derivatives to access all-carbon quaternary stereocenters. Broad functional group tolerance, high yield, and high and stereochemical fidelity are observed. Our mechanistic investigations will also be presented.

Stereospecific synthesis of all-carbon quaternary centers via C–O bond activation

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.