A Practical One-Pot Synthesis of 5-Aryl-2-furaldehydes

Abstract

A useful one-pot synthesis of 5-aryl-2-furaldehydes via palladium-mediated Suzuki coupling of aryl halides with in situ generated 5-(diethoxymethyl)-2-furylboronic acid is described. The procedure has general applicability, delivers high yields, and is amenable to scale-up.

Pd/C: An Old Catalyst for New Applications – Its Use for the Suzuki–Miyaura Reaction

“…Although one report has described [15] the use of NEt 3 , inorganic bases such as Na 2 CO 3 , K 2 CO 3 , Cs 2 CO 3 or Na 3 PO 4 are the most efficient for Suzuki-Miyaura crosscoupling reactions. For sensitive substrates bearing hydrolysable ester functions, the use of KF could be of particular interest.…”

Development of the Applications of Palladium on Charcoal in Organic Synthesis

“…It is still a challenge, however, to use Pd/C as catalyst for the synthesis of heterocyclic biaryl derivatives. Based on previous studies, Sajiki and co‐workers reported a ligand‐free and heterogeneous Pd/C‐catalyzed hetero‐Suzuki–Miyaura coupling reaction with a wide range of heteroaryl substrates ,. The system is suitable for both heterocyclic‐alicyclic and heterocyclic‐biaryl derivatives with good yields.…”

Five‐Membered Heterocycles: Furan

“…Slow addition of aryl halides to the reaction mixture avoids the homocoupling efficiently [72]. A one-pot Suzuki coupling of aryl halides with in situ generated 5-(diethoxymethyl)-2-furylboronic acid catalyzed by palladium(0) also gave 5-aryl-2-furaldehydes in high yields [73]. A simple procedure to prepare 5-aryl-and 5-pyridyl-2-furaldehydes from the inexpensive and commercially available 2-furaldehyde diethyl acetal through direct lithiation-transmetallation-electrophile trapping has been reported.…”