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)and#8208;promoted, bidentate ligandand#8208;assisted regioselective Cand#8722;H activation/arylation of the Cand#8208;3 position of 2and#8208; or 3and#8208;(aminoalkyl)and#8208;thiophene and furfurylamine derivatives with various aryland#8208;/heteroaryl iodides was reported. Various aryland#8208;/heteroaryl iodides and bidentate ligands, such as, picolinamide, quinolineand#8208;2and#8208;carboxamide, pyrazineand#8208;2and#8208;carboxamide and oxalylamide were examined for accomplishing the regioselective palladium(II)and#8208;promoted Cand#8722;H arylation and Cand#8722;C bond formation at the Cand#8208;3 position of the 2and#8208;/3and#8208;(aminoalkyl)and#8208;thiophene and furfurylamine derivatives. The Xand#8208;ray structures of the regioisomers 8and#8201;c and 9and#8201;c confirmed the observed regiselectivity. This Cand#8722;H activation/arylation method gave an access to several C3and#8208;arylated 2/3and#8208;(aminoalkyl)and#8208;thiopheneand#8208; and furfurylamine based biaryl scaffolds that are analogous to biologically active C3and#8208;arylated 2/3and#8208;(aminoalkyl)and#8208;thiophenes and furfurylamines. newline