Towards Iron‐Catalyzed Sonogashira Cross‐Coupling Reactions. Issue 11 (22nd July 2016)

• Record Type: Journal Article
• Authors: Petuker, Anette; El‐Tokhey, Mohamed; Reback, Matthew L.; Mallick, Bert; Apfel, Ulf‐Peter
• Is Part Of: ChemistrySelect. Volume 1:Issue 11(2016)
• Page Start: 2717
• Page End: 2721
• Publication Date: 2016-07-22
• Subjects: Iron -- Diphosphine ligands -- Sonogashira cross-coupling -- Catalysis -- Acetylenes; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201600771
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Herein we report on the selective iron‐catalyzed cross‐coupling reaction of terminal phenylacetylenes with iodo‐aryl derivatives to afford the respective coupling products in the presence of 10 mol% FeCl2 (bdmd) and 10 mol% [Cu(CH3 CN)4 ]BF4 (bdmd=bis((diphenylphosphanyl)methyl)diphenylsilane). The yields are moderate to good in 1, 4‐dioxane or DMF. This is the first example of a well‐defined and fully analysed ferrous complex acting as a precatalyst in Sonogashira cross‐coupling reactions. Notably, FeCl2 (bdmd) is compatible with reactive substituents such as carbonyl‐, carboxyl‐, hydroxy‐, and amino‐groups, which allows for an effective cross‐coupling reaction in the presence of such functional groups. Abstract : Herein we report on Ph2 Si(CH2 PPh2 )2 FeCl2, a well‐defined precatalyst for Sonogashira cross‐coupling reactions that is compatible with reactive substituents such as carbonyl‐ carboxyl‐, hydroxyl‐, and amino‐groups.