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

被引：41

作者：

Maddock, Lewis C. H. ^{[1
]}

Nixon, Tracy ^{[1
]}

Kennedy, Alan R. ^{[1
]}

Probert, Michael R. ^{[2
]}

Clegg, William ^{[2
]}

Hevia, Eva ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[2] Newcastle Univ, Sch Nat & Environm Sci, Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 01期

关键词：

alkali metals; C-F bond activation; iron; metalation; mixed-metal chemistry; GAS-PHASE; COMPLEXES; FLUOROCARBONS; 2-COORDINATE; MOLECULES; BENZENE; ACIDITY; IRON;

D O I：

10.1002/anie.201709750

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pairing iron bis(amide) Fe(HMDS)(2) with Na(HMDS) to form new sodium ferrate base [(dioxane)(0.5)center dot 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 degrees 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.

引用

页码：187 / 191

页数：5

共 33 条

[1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks [J].