Utilising Sodium‐Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C−H and C−F Bond Activations | Zendy

Maddock Lewis C. H. | Zendy; Nixon Tracy | Zendy; Kennedy Alan R. | Zendy; Probert Michael R. | Zendy; Clegg William | Zendy; Hevia Eva | Zendy

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Utilising Sodium‐Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C−H and C−F Bond Activations

Author(s) -

Maddock Lewis C. H.,

Nixon Tracy,

Kennedy Alan R.,

Probert Michael R.,

Clegg William,

Hevia Eva

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201709750

Subject(s) - regioselectivity , chemistry , sodium , amide , triple bond , medicinal chemistry , stereochemistry , combinatorial chemistry , polymer chemistry , double bond , organic chemistry , catalysis

Pairing iron bis(amide) Fe(HMDS) 2 with Na(HMDS) to form new sodium ferrate base [(dioxane) 0.5 ⋅NaFe(HMDS) 3 ] ( 1 ) enables regioselective mono and di‐ferration (via direct Fe−H exchange) of a wide range of fluoroaromatic substrates under mild reaction conditions. Trapping of several ferrated intermediates has provided key insight into how synchronised Na/Fe cooperation operates in these transformations. Furthermore, using excess 1 at 80 °C switches on a remarkable cascade process inducing the collective twofold C−H/threefold C−F bond activations, where each C−H bond is transformed to a C−Fe bond whereas each C−F bond is transformed into a C−N bond.

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