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Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2014

Resorcinarenyl-Phosphines in Suzuki-Miyaura CrossCoupling Reactions of Aryl Chlorides

Résumé

Two phosphines built on a bowl-shaped resorcin[4]arene skeleton, namely 5-diphenylphosphanyl- and 5-diisopropylphosphanyl-4(24),6(10),12(16),18(22)-tetramethylenedioxy-2, 8,14,20-tetrapentylresorcin[4]arene, have been synthesised and tested in the Suzuki-Miyaura cross-coupling reaction of aryl halides. Combining these ligands with [Pd(OAc)(2)] resulted in highly active catalysts that allowed the formation of o,o-biphenyls starting from aryl chlorides. The remarkable activities observed possibly arise from 1) the capacity of the phosphines to operate transiently as P,O chelators, thereby increasing the electron density of the metal, and 2) the ability of the ligands to embed metal-organic units, which, when occurring, makes the ligand considerably bulkier so as to disfavour the coordination of a second phosphine. Both features are known to facilitate the oxidative addition step.

Dates et versions

hal-01063265 , version 1 (11-09-2014)

Identifiants

Citer

Laure Monnereau, Hani El Moll, David Semeril, Dominique Matt, Loic Toupet. Resorcinarenyl-Phosphines in Suzuki-Miyaura CrossCoupling Reactions of Aryl Chlorides. European Journal of Inorganic Chemistry, 2014, 2014 (8), pp.1364-1372. ⟨10.1002/ejic.201301473⟩. ⟨hal-01063265⟩
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