New organometallic Schiff-base copper complexes as efficient "click" reaction precatalysts. (16th February 2016)

• Record Type: Journal Article
• Authors: Liu, Xiang; Novoa, Néstor; Manzur, Carolina; Carrillo, David; Hamon, Jean-René
• Is Part Of: New journal of chemistry. Volume 40:Number 4(2016:Apr.)
• Page Start: 3308
• Page End: 3313
• Publication Date: 2016-02-16
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c5nj02681d
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : In the presence of sodium ascorbate, recyclable CuAAC precatalysts displayed high activity allowing the synthesis of a wide variety of 1, 4-disubstituted 1, 2, 3-triazoles in high isolated yields. Abstract : A new ferrocenyl-containing unsymmetrical Cu II -Schiff-base complex, 2, and its covalently poly(methyl) (methacrylate) (PMMA)-grafted counterpart3 were synthesized and characterized using elemental analysis, electrospray ionisation (ESI) mass spectrometry for2, and FT-IR spectroscopy. New complex3 was employed as a precatalyst in the copper-catalyzed [3+2] cycloaddition of organic azides to alkynes (CuAAC, "click" reaction). The active Cu I species generated from only 0.2 mol% of Cu II precatalyst2 and sodium ascorbate displayed high activity at room temperature in ethanol for 24 hours allowing the synthesis of a wide variety of 1, 4-disubstituted 1, 2, 3-triazoles in high isolated yields. The PMMA-supported catalyst3 is also efficient and has been reused at least three times in these "click" reactions without any loss of activity or copper leaching.