Convenient access to readily soluble symmetrical dialkyl-substituted α-oligofurans

Edward E. Korshin, Gregory M. Leitus, Michael Bendikov

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


An expedient approach to the synthesis of well soluble symmetrical dialkyl-substituted α-oligofurans containing up to 8 π-conjugated furan heterocycles is reported. An ultimate symmetry and high solubility of these α-oligofurans were guaranteed using the 3,3′-diheptyl-2,2′- bifuran core and its symmetrical elongation through Suzuki-Miyaura or Stille cross-couplings. 3,3′-Diheptyl-2,2′-bifuran was prepared from 2,2′-bifuran-3,3′-dicarbaldehyde by the Wittig olefination and subsequent Pd/C-catalyzed transfer hydrogenation. The most appropriate access to 2,2′-bifuran-3,3′-dicarbaldehyde was achieved through a regioselective lithiation of 3-furanaldehyde acetal followed by CuCl 2-induced homocoupling and deprotection. Single crystal X-ray analysis of 2,2′-bifuran-3,3′-dicarbaldehyde revealed anti-arrangement of the furan rings in planar molecules and an unexpected tight herringbone-type packing in crystals. This journal is

Original languageEnglish
Pages (from-to)6661-6671
Number of pages11
JournalOrganic and Biomolecular Chemistry
Issue number34
StatePublished - 14 Sep 2014
Externally publishedYes


Dive into the research topics of 'Convenient access to readily soluble symmetrical dialkyl-substituted α-oligofurans'. Together they form a unique fingerprint.

Cite this