Palladium catalyzed direct coupling of 5-bromo-2-furaldehyde with furfural and thiophene derivatives. Issue 45 (9th November 2016)

• Record Type: Journal Article
• Authors: Kainulainen, Tuomo P.; Heiskanen, Juha P.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 45(2016)
• Page Start: 5012
• Page End: 5016
• Publication Date: 2016-11-09
• Subjects: Direct coupling -- Furfural -- Heteroaromatic compounds -- Palladium catalyst; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.097
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Direct coupling of 5-bromo-2-furaldehyde with heteroaromatic compounds. The 2-furaldehyde subunit can be produced from biomass resources. The aldehyde groups offer reactive sites for further modification. Abstract: A direct coupling approach for the synthesis of 5, 5′-bisfurfural via the coupling of 2-furaldehyde (furfural) and 5-bromo-2-furaldehyde using the air-stable catalyst Pd(OAc)2 and the air-stable ligand P( t -Bu)3 HBF4 was examined. The developed procedure was used to functionalize thiophene containing moieties commonly found in organic electronics. The aromatic CH bond activated coupling with 5-bromo-2-furaldehyde afforded novel compounds with useful 5-heteroaryl-2-furaldehyde type functionality.