Alumina‐Supported Copper Iodide: An Efficient and Recyclable Catalyst for Microwave‐Assisted Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via Three‐Component Reaction in Water

Abstract

Ao ne-pot procedure fort he synthesis of 1,4-disubstituted 1,2,3-triazoles by at hree-component reactiono f allyl or benzyl halides, sodiuma zide, and terminal alkynes over an eutral alumina-supported copper iodide catalyst has been developed. The products were isolated by simple filtration followed by washing of the catalystw ith acetone. The products were obtained in almost pure form in up to 98 % yield (TON 495). The catalystc an be recycled for more than eight subsequent reactions. The halides are directly converted into triazoles via in situ formation of azides and thus han-dling of hazardousa zides can be avoided. The broad scope of this protocol is shown by the synthesis of av ariety of diverselys ubstituted 1,2,3-triazoles and also two-component azide-alkyne click reaction. The key features of this procedure are the use of water as as olvent, recyclability of the catalystu pt oe ight runs without appreciable loss of activity, and high yields of products.T he catalysth as been fully characterized by FTIR, solid-state NMR and EDX spectroscopy, ESEM, TGA, and XRD.[a] S.

New functionalization of graphene oxide with N2O2ligand for efficient loading of Cu nanostructures as a heterogeneous nanocatalyst for the synthesis of β‐hydroxy‐1,2,3‐triazoles

“…Recently, copper has been immobilized on various supports for the synthesis of triazole derivatives . Agalave et al [15a].…”

“…Recently, copper has been immobilized on various supports for the synthesis of triazole derivatives . Agalave et al [15a]. supported copper iodide on alumina and used it for the synthesis of 1,2,3‐triazole derivatives using microwave irradiation in water.…”

“…Due to the heterogeneous behavior of the catalyst, those authors recycled it in more than eight subsequent reactions. Ebadi et al [15e]. anchored a copper catalyst on functionalized magnetic nanoparticles and then investigated its application for the synthesis of 1,4‐disubstituted 1,2,3‐triazole derivatives through click reactions.…”

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

“…Although details of the preparation and structure are not entirely clear, Agalave et al reported the use of CuI on bare neutral alumina as a cost-effective supported CuAAC catalyst [131]. The material was used in the reactions of activated halides (Scheme 2a) or a few preformed azides (Scheme 1), in water or DMF-water (4:1) with microwave (MW) or ultrasound (US) irradiation.…”

Highly Stable Copper Nanoparticles Linked to Organic Frameworks as Recyclable Catalyst for Three‐Component Click Cycloaddition in Water

“…Recently reported catalysts for click reactions with high TOF include, dendrimer nanoreactor for part‐per‐million Cu 1 catalyst (TON =510000, TOF=21200 h −1 ), amphiphilic Cu 1 catalyst (TON=86000, TOF 3600 h −1 ) for two component click reaction and alumina supported CuI (TON=495, TOF=4950 h −1 ) for three component click reactions. The TOF and TON values obtained with our catalyst for both two‐component (Table ) and three‐component reactions (Table , Table S6 and Table S7) are comparable and even higher than the recently reported values…”