Photocatalytic Indole Diels-Alder Cycloadditions Mediated by Heterogeneous Platinum-Modified Titanium Dioxide

ACS Catalysis
Spencer P PitreTehshik P Yoon

Abstract

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.

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Citations

Nov 15, 2019·Organic & Biomolecular Chemistry·Haojie Cheng, Wentao Xu
Dec 19, 2020·Organic & Biomolecular Chemistry·Chun-Ting HeBang-Guo Wei
Feb 12, 2021·Organic & Biomolecular Chemistry·Tohasib Yusub Chaudhari, Vibha Tandon
Mar 27, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yohei Okada
Apr 17, 2018·The Journal of Organic Chemistry·Yohei OkadaHidehiro Kamiya
Mar 28, 2019·Organic Letters·Kaii NakayamaYohei Okada
Jul 3, 2018·Journal of the American Chemical Society·Michael J JamesFrank Glorius
Mar 22, 2019·Journal of the American Chemical Society·Elliot P FarneyTehshik P Yoon
Dec 20, 2018·Journal of the American Chemical Society·Spencer P PitreLarry E Overman
Sep 19, 2020·Journal of the American Chemical Society·Qilei Zhu, Daniel G Nocera
Jul 20, 2019·The Journal of Organic Chemistry·Kenta TanakaKiyoshi Honda

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