Oxidative Addition of 1,3-Dicarbonyl Compounds to Terminal Acetylenes Mediated by Cerium(IV) Ammonium Nitrate

Abstract

Cerium(IV) ammonium nitrate mediated oxidative addition of 1,3-dicarbonyl compounds to terminal acetylenes to yield multisubstituted furan derivatives is reported here. The simplicity of the reaction and the ease of execution are particularly noteworthy.

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

“…279 Very recently, an oxidative CAN-mediated synthesis of 3-hydroxyfurans from terminal alkynes and 1,3-dicarbonyl compounds was reported by Deepthi et al 280 …”

“…Fe(III)-, Zn-, or In(III)-catalyzed "3 + 2" reactions that feature Michael addition/cyclocondensation cascade between 1,3-dicarbonyl compounds and but-2-ene-1,4-diones to provide tetrasubstituted furans were reported by Jaisankar and coworkers. 279 Very recently, an oxidative ceric ammonium nitrate (CAN)-mediated synthesis of 3-hydroxyfurans from terminal alkynes and 1,3-dicarbonyl compounds was reported by Deepthi et al 280 Komeyama and Takaki disclosed an interesting approach toward furans 2-583 via the Bi(III)-catalyzed fomal [3 + 2] reaction of 1,3-dicarbonyl compounds 2-581 with acyloins 2-582. The reaction proceeds via the formation of 1,4-diketone intermediate followed by a cyclocondensation to give furan 2-583 (Scheme 166).…”

“…Fe(III)-, Zn-, or In(III)-catalyzed “3 + 2” reactions that feature Michael addition/cyclocondensation cascade between 1,3-dicarbonyl compounds and but-2-ene-1,4-diones to provide tetrasubstituted furans were reported by Jaisankar and co-workers . Very recently, an oxidative ceric ammonium nitrate (CAN)-mediated synthesis of 3-hydroxyfurans from terminal alkynes and 1,3-dicarbonyl compounds was reported by Deepthi et al…”