Copper-Catalyzed Domino Rearrangement/Dehydrogenation Oxidation/Carbene Oxidation for One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans

Abstract

A novel and efficient method for the regiospecific synthesis of polysubstituted furan aldehydes/ketones has been developed via a copper(I)-catalyzed rearrangement/dehydrogenation oxidation/carbene oxidation sequence of 1,5-enynes in situ formed from alkynols and diethyl but-2-ynedioate under atmospheric pressure. The domino reaction proceeds smoothly under mild conditions with commercially available catalysts and affords highly functionalized furans in moderate to good yields.

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

“…255 A variety of propargyl alcohol-possessing alkyl- and aryl substituents could be employed in this reaction providing furan products in moderate to good yields. However, the reaction is limited to diethyl acetylenedicarboxylate, as the use of other alkynoates resulted in no product formation.…”

Metal-catalyzed Furan Synthesis. A Review

“…The cyclization of propargyl vinyl ethers has also received considerable attention with several different metal catalysts being utilized for the preparation of furans, including Cu 83,84 and Au. 85,86 Jiang has recently published an Fe-catalyzed process which generally gives good yields of furans and requires a relatively inexpensive catalyst (Scheme 34).…”

Preparation of 3,4,5-substituted furan-2(5H)-ones using aluminum hydrogen sulfate as an efficient catalyst

“…MCRs based on the use of acetylenic esters as starting material has gained much importance in organic synthesis, partly because of the diverse types of clinical and pharmacological activity associated with the products of this reaction [2][3][4][5][6]. Of all kinds of MCRs based on the use of acetylenic esters, methods to synthesize furan derivatives were considered as the most versatile ones for chemical construction of poly-substituted furans [7][8][9][10][11].…”