Palladium(II)‐Promoted Directing Group‐Enabled Regioselective C‐H Arylation of The C‐3 Position of 2‐ or 3‐(Aminoalkyl)‐Thiophene and Furfurylamine Derivatives

Abstract

The palladium(II)‐promoted, bidentate ligand‐assisted regioselective C−H activation/arylation of the C‐3 position of 2‐ or 3‐(aminoalkyl)‐thiophene and furfurylamine derivatives with various aryl‐/heteroaryl iodides was reported. Various aryl‐/heteroaryl iodides and bidentate ligands, such as, picolinamide, quinoline‐2‐carboxamide, pyrazine‐2‐carboxamide and oxalylamide were examined for accomplishing the regioselective palladium(II)‐promoted C−H arylation and C−C bond formation at the C‐3 position of the 2‐/3‐(aminoalkyl)‐thiophene and furfurylamine derivatives. The X‐ray structures of the regioisomers 8 c and 9 c confirmed the observed regiselectivity. This C−H activation/arylation method gave an access to several C3‐arylated 2/3‐(aminoalkyl)‐thiophene‐ and furfurylamine based biaryl scaffolds that are analogous to biologically active C3‐arylated 2/3‐(aminoalkyl)‐thiophenes and furfurylamines.