We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.
A visible-light mediated three-component radical process using dithiocarbamate anion catalysis / Cuadros S.; Horwitz M.A.; Schweitzer-Chaput B.; Melchiorre P.. - In: CHEMICAL SCIENCE. - ISSN 2041-6520. - ELETTRONICO. - 10:21(2019), pp. 5484-5488. [10.1039/c9sc00833k]
A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
Melchiorre P.
Ultimo
Supervision
2019
Abstract
We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
