Bimetallic Cu/Pd Catalysts with Bridging Aminopyrimidinyl Phosphines for Decarboxylative Cross‐Coupling Reactions at Moderate Temperature. Issue 21 (17th September 2015)

• Record Type: Journal Article
• Authors: Hackenberger, Dagmar; Song, Bingrui; Grünberg, Matthias F.; Farsadpour, Saeid; Menges, Fabian; Kelm, Harald; Groß, Cedric; Wolff, Timm; Niedner‐Schatteburg, Gereon; Thiel, Werner R.; Gooßen, Lukas J.
• Is Part Of: ChemCatChem. Volume 7:Issue 21(2015:Nov.)
• Page Start: 3579
• Page End: 3588
• Publication Date: 2015-09-17
• Subjects: bridging ligands -- carboxylic acids -- copper -- cross-coupling -- palladium; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201500769
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A bimetallic catalyst system is presented that enables the decarboxylative cross‐coupling of triflates with carboxylate salts at only 100 °C, which is 70 °C lower than with previous Cu/Pd‐based systems. The new protocol allows the coupling of a broad range of aryl triflates with various substituted 2‐nitrobenzoates in good to excellent yields. The key feature of the catalyst system is a bidentate P, N‐ligand designed to bridge the Pd and Cu centres and thereby facilitating the rate‐determining transmetalation step. Mass spectrometry (ESI‐MS) studies support the ability of the aminopyrimidinyl phosphine to simultaneously coordinate copper and palladium. Abstract : Turning down the heat : A Cu/Pd‐based catalyst system is presented that enables the decarboxylative cross‐coupling of triflates with carboxylate salts at only 100 °C. The key feature of the catalyst system is a bidentate P, N‐ligand designed to bridge the Pd and Cu centres, thereby facilitating the rate‐determining transmetalation step.