Indole alkaloids represent an important class of molecules, with many naturally occurring derivatives possessing significant biological activity. One area that requires further development in the synthesis of indole derivatives is the Diels-Alder reaction. In this work, we expand on our previously developed heterogeneous protocol for the [4+2] cycloaddition of indoles and electron-rich dienes mediated by platinum nanoparticles supported on titanium dioxide semiconductor particles (Pt(0.2%)@TiO2) with visible-light irradiation. This reaction proceeds with broad scope and is more efficient per incident photon than the previous homogeneous method, and the catalyst can be easily recycled and reused.
Keywords: Diels–Alder reactions; Heterogeneous catalysis; Indoles; Photoredox catalysis; Radical-cation cycloadditions.