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Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

ABSTRACT: A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp3 )-(sp3 ) and C(sp3 )-H bond cleavage gives access to distal carbon radicals that undergo SH 2 functionalisations. These mild, visible-light-mediated procedures can be used for remote fluorination, chlorination, and azidation, and were applied to the modification of bioactive and structurally complex molecules.

SUBMITTER: Dauncey EM

PROVIDER: S-EPMC5814920 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

Dauncey Elizabeth M EM Morcillo Sara P SP Morcillo Sara P SP Douglas James J JJ Sheikh Nadeem S NS Leonori Daniele D

Angewandte Chemie (International ed. in English) 20171204 3

A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp3 )-(sp3 ) and C(sp3 )-H bond cleavage gives access to distal carbon radicals that undergo SH 2 functionalisations. These mild, visible-light-mediated procedures can be used for remote fluorination, chlorination, ...[more]

PMID: 29114978

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