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.
Decatungstate-Mediated C(sp(3))-H Heteroarylation via Radical-Polar Crossover in Batch and Flow / Wan, T; Capaldo, L; Laudadio, G; Nyuchev, Av; Rincon, Ja; Garcia-Losada, P; Mateos, C; Frederick, Mo; Nuno, M; Noel, T. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 60:33(2021), pp. 17893-17897. [10.1002/anie.202104682 EA JUL 2021]
Decatungstate-Mediated C(sp(3))-H Heteroarylation via Radical-Polar Crossover in Batch and Flow
Capaldo L;
2021-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
