Construction of C(sp2)-C(sp3) bonds is relatively difficult in comparison to C(sp2)-C(sp2) bonds. Recently, photoredox catalytic and other photochemical methodologies, together with technological achievements expanded the scope of C(sp2)-C(sp3) bond constructions.<br/>In particular, the Minisci reaction is a synthetically useful tool for the functionalization of heterocycles, nevertheless, it sometimes suffers from harsh conditions, low yields and selectivities. Building on batch results obtained in our multifunctional photoreactor we devised a continuous microflow procedure. In this an in situ formed N-(acyloxy)phthalimide esters (NAP) in combination with transition metal based photoredox catalysts or organic dyes were employed for the alkylation of six- and five-membered heteroaromatic ring systems. The flow procedure allowed for the convenient integration of NAP intermediate formation and the C(sp2)-C(sp3) coupling reaction. Subsequent reduction of the Minisci products gave access to novel heterocycles with even higher 3D character. The hydrogenations were carried out in automated flow systems affording the products in good stereoselectivities.

Synthesis of substituted heteroarenes and their subsequent reduction using flow technology to produce novel heterocycles

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.