Details

Autor(en) / Beteiligte

• Elaieb, Fethi
• Hedhli, Ahmed
• Sémeril, David
• Matt, Dominique

Titel

Arylcalixarenyl Phosphines in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions

Ist Teil von

• European journal of organic chemistry, 2016-04, Vol.2016 (10), p.1867-1873

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2016

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Two electron‐rich arylcalixarenylphosphines have been synthesized in three steps from the appropriate 5‐bromocalix[4]arene precursor 1. 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 ligand 6 had a higher activity that that of 5, and the structures of ligand 5 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. 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.