Litcius/Paper detail

Synthesis of Ferrocene 1,3‐Derivatives by Distal C−H Activation**

Princi Gupta, Suchithra Madhavan, Manmohan Kapur

2023Angewandte Chemie International Edition11 citationsDOI

Abstract

Abstract The third position of cyclopentadienyl ring of a monosubstituted ferrocene has remained as an inaccessible chemical space for direct functionalization. Until recently, functionalizing the C(3)‐position while bypassing the predominantly active C(2)‐position is the most challenging task. Herein, we report a distal C−H functionalization of monosubstituted ferrocenes using an easily removable directing group with precise site‐selectivity, under a Pd II / mono‐ N ‐protected amino‐acid ligand catalytic system. The robust synthetic protocol leads to the synthesis of ferrocene 1,3‐derivatives with broad scope in olefins while functionalizing ferrocenyl methylamine in moderate to good yields via a highly strained ferrocene appended 12‐membered palladacycle intermediate.

Topics & Concepts

FerroceneCyclopentadienyl complexChemistrySurface modificationCombinatorial chemistryMethylamineLigand (biochemistry)Ring (chemistry)CatalysisReactivity (psychology)SelectivityOrganic chemistryReceptorElectrochemistryBiochemistryAlternative medicineMedicinePhysical chemistryPathologyElectrodeFerrocene Chemistry and ApplicationsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions