Arylcalixarenyl Phosphines in Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling Reactions. Issue 10 (10th March 2016)

• Record Type: Journal Article
• Authors: Elaieb, Fethi; Hedhli, Ahmed; Sémeril, David; Matt, Dominique
• Is Part Of: European journal of organic chemistry. Issue 10(2016)
• Page Start: 1867
• Page End: 1873
• Publication Date: 2016-03-10
• Subjects: Calixarenes -- Phosphane ligands -- Cross‐coupling -- Palladium -- Gold; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600055
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Two electron‐rich arylcalixarenylphosphines have been synthesized in three steps from the appropriate 5‐bromocalix[4]arene precursor1 . The combination of 5‐(2‐diisopropylphosphinophenyl)‐25, 26, 27, 28‐tetrapropyloxycalix[4]arene (5 ) and 5‐(2‐dicyclohexylphosphinophenyl)‐25, 26, 27, 28‐tetrapropyloxycalix[4]arene (6 ), respectively, with [Pd2 (dba)3 ] (dba = dibenzylideneacetone) generated effective catalysts for the cross‐coupling reactions of hindered aryl chlorides and arylboronic acids. Dicyclohexylphosphino‐substituted ligand6 had a higher activity that that of5, and the structures of ligand5 and [AuCl·5 ] were determined by single‐crystal X‐ray diffraction studies. The solid‐state structure of [AuCl·5 ] revealed that the gold atom lies above the outer face of the calixarene unit, with distances of 3.08 and 3.28 Å between the gold atom and the two closest aromatic carbon atoms of the calixarene moiety. Abstract : The first biaryl monophosphines with a calix[4]arene skeleton have been prepared. These arylcalixarenylphosphines in combination with [Pd2 (dba)3 ] (dba = dibenzylideneacetone) effectively catalyzed the cross‐coupling reactions of hindered aryl chlorides and aryl boronic acids.