Iron-Catalysed C( sp 2 )-H Borylation Enabled by Carboxylate Activation

Arene C( )-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying...

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Published inMolecules (Basel, Switzerland) Vol. 25; no. 4; p. 905
Main Authors Britton, Luke, Docherty, Jamie H, Dominey, Andrew P, Thomas, Stephen P
Format Journal Article
LanguageEnglish
Published Switzerland MDPI 18.02.2020
MDPI AG
Subjects
borylation
c-h functionalisation
catalysis
iron
photochemistry
pinacolborane
pinacolborane
catalysis
Iron
photochemistry
C-H functionalisation
borylation
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Summary:Arene C( )-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C( )-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25040905