Cellulose-Supported Heterogeneous Gold-Catalyzed Cycloisomerization Reactions of Alkynoic Acids and Allenynamides

Luca Deiana; Elham Badali; Abdolrahim A Rafi; Cheuk-Wai Tai; Jan-E Bäckvall; Armando Córdova

doi:10.1021/acscatal.3c02722

Cellulose-Supported Heterogeneous Gold-Catalyzed Cycloisomerization Reactions of Alkynoic Acids and Allenynamides

ACS Catal. 2023 Jul 25;13(15):10418-10424. doi: 10.1021/acscatal.3c02722. eCollection 2023 Aug 4.

Authors

Luca Deiana¹, Elham Badali¹, Abdolrahim A Rafi¹, Cheuk-Wai Tai², Jan-E Bäckvall^{1

3}, Armando Córdova¹

Affiliations

¹ Department of Natural Sciences, Mid Sweden University, Holmgatan 10, SE-85179 Sundsvall, Sweden.
² Department of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
³ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.

Abstract

Herein, we describe efficient nanogold-catalyzed cycloisomerization reactions of alkynoic acids and allenynamides to enol lactones and dihydropyrroles, respectively (the latter via an Alder-ene reaction). The gold nanoparticles were immobilized on thiol-functionalized microcrystalline cellulose and characterized by electron microscopy (HAADF-STEM) and by XPS. The thiol-stabilized gold nanoparticles (Au⁰) were obtained in the size range 1.5-6 nm at the cellulose surface. The robust and sustainable cellulose-supported gold nanocatalyst can be recycled for multiple cycles without losing activity.