Tetrahedron letters

Suzuki route to regioregular polyalkylthiophenes using Ir-catalysed borylation to make the monomer, and Pd complexes of bulky phosphanes as coupling catalysts for …

IA Liversedge, SJ Higgins, M Giles, M Heeney…

Index: Liversedge, Iain A.; Higgins, Simon J.; Giles, Mark; Heeney, Martin; McCulloch, Iain Tetrahedron Letters, 2006 , vol. 47, # 29 p. 5143 - 5146

Full Text: HTML

Citation Number: 44

Abstract

We have applied palladium complexes of bulky, electron-rich phosphane ligands as catalysts for the Suzuki synthesis of highly head-to-tail regioregular polyalkylthiophenes from 2-(5-bromo-4-n-alkyl-thiophen-2-yl)-4, 4, 5, 5-tetramethyl-[1, 3, 2] dioxaborolane. The monomer can be prepared in high yield by Ir-catalysed borylation of 2-bromo-3- hexylthiophene, without the need for organolithium reagents or strong bases.