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Decatungstate-Mediated C(sp³ )-H Heteroarylation via Radical-Polar Crossover in Batch and Flow.

ABSTRACT: Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp³ )-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(sp³ )-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.

SUBMITTER: Wan T

PROVIDER: S-EPMC8457183 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Decatungstate-Mediated C(sp3 )-H Heteroarylation via Radical-Polar Crossover in Batch and Flow.

Wan Ting T Capaldo Luca L Laudadio Gabriele G Nyuchev Alexander V AV Rincón Juan A JA García-Losada Pablo P Mateos Carlos C Frederick Michael O MO Nuño Manuel M Noël Timothy T

Angewandte Chemie (International ed. in English) 20210709 33

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3 )-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(sp3 )-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuo ...[more]

PMID: 34060204

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