In nature and medicine, structural complexity often relates to the utility of a molecule (e.g. N- and O-substituents are often found in antibiotics and anticancer treatment).  Furthermore, one of the most common motifs in drug discovery is 1,2-amino alcohol (or β-amino alcohol); and one method to achieve this substrate class is to utilize allylic alcohols as precursor for alkene difunctionalization. Previously, our group have reported a procedure to convert allylic alcohols into oxazolines by N-radical. The N-centered radical is generated via single electron transfer with a reducing Ir photocatalyst under visible light. However, the subsequent alkyl radical is limited by electrophilic radical traps to efficiently terminate the reaction due to radical polarity. Inspired by G. Liu’s contributions to generate and capture C-radical using Cu catalysts, we envisioned that a merger of two strategies can significantly expand the scope of amino-functionalizations on allylic alcohols. Introducing the Cu catalyst into the existing system, however, can interfere the electron transfer reduction to generate N-radical. Hence, we develop a novel method to harness N-radical via energy transfer with an Ir photosensitizer, to avoid the reductive side pathway with Cu catalyst.

Facile synthesis of β-amino alcohols via energy transfer

ACS Spring 2022

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