Copper‐Catalysed Suzuki‐Miyaura Cross‐Coupling of Highly Fluorinated Aryl Boronate Esters with Aryl Iodides and Bromides and Fluoroarene−Arene π‐Stacking Interactions in the Products. Issue 21 (8th August 2019)

• Record Type: Journal Article
• Authors: Budiman, Yudha P.; Friedrich, Alexandra; Radius, Udo; Marder, Todd B.
• Is Part Of: ChemCatChem. Volume 11:Issue 21(2019)
• Page Start: 5387
• Page End: 5396
• Publication Date: 2019-08-08
• Subjects: homogeneous catalysis -- boron -- boronate -- fluorine -- fluoroarene; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201901220
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A combination of copper iodide and phenanthroline as the ligand is an efficient catalyst for Suzuki‐Miyaura cross‐coupling of highly fluorinated boronate esters (aryl−Bpin) with aryl iodides and bromides to generate fluorinated biaryls in good to excellent yields. This method represents a nice alternative to traditional cross‐coupling methods which require palladium catalysts and stoichiometric amounts of silver oxide. We note that π⋅⋅⋅π stacking interactions dominate the molecular packing in the partly fluorinated biaryl crystals investigated herein. They are present either between the arene and perfluoroarene, or solely between arenes or perfluoroarenes, respectively. Abstract : Cheap and less toxic ! We introduce an alternative for Suzuki‐Miyaura cross‐coupling reactions of challenging substrates, namely highly fluorinated aryl−boronate esters, with aryl iodides or bromides using Cu I /phenanthroline as the catalyst precursor to generate fluorinated biaryls in good to excellent yields. Crystals of the products show a diverse range of interesting π‐stacking interactions.