Ting Wan1, Luca Capaldo2, Gabriele Laudadio2, Alexander Nyuchev3, Juan Rincon4, Pablo Garcia-Losada4, Carlos Mateos Gutierrez4, Michael O Frederick5, Manuel Nuno6, Timothy Noel7. 1. University of Amsterdam Van 't Hoff Institute for Molecular Sciences: Universiteit van Amsterdam Van 't Hoff Institute for Molecular Sciences, Chemistry, BELGIUM. 2. University of Amsterdam Van 't Hoff Institute for Molecular Sciences: Universiteit van Amsterdam Van 't Hoff Institute for Molecular Sciences, chemistry, NETHERLANDS. 3. Technische Universiteit Eindhoven, chemistry, NETHERLANDS. 4. Eli Lilly and Company, R&D, SPAIN. 5. Eli Lilly and Company, R&D, UNITED STATES. 6. Vapourtec Ltd, R&D, UNITED KINGDOM. 7. University of Amsterdam, Van't Hoff Institute for Molecular Science, PO Box 94157, Science Park 904, 1090 GD, Amsterdam, NETHERLANDS.
Abstract
Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp 3 )-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative Radical-Polar Crossover concept to access the direct net-oxidative C(sp 3 )-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin and dideoxyribose.
Photocatalytic hydrogen atom transfer is a very pon class="Chemical">werful strategy for the regioselective C(sp 3 )-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstatehydrogen atom transfer photocatalysis with the oxidative Radical-Polar Crossover concept to access the direct net-oxidative C(sp 3 )-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin and dideoxyribose.
Authors: Ting Wan; Zhenghui Wen; Gabriele Laudadio; Luca Capaldo; Rob Lammers; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Rémy Broersma; Timothy Noël Journal: ACS Cent Sci Date: 2021-12-16 Impact factor: 14.553