Fast Suzuki-Miyaura cross-coupling reaction with hexacationic triarylphosphine Bn-Dendriphos as ligand

D.J.M. Snelders, R. Kreiter, J.J. Firet, G. van Koten, R.J.M. Klein Gebbink

Research output: Contribution to journalArticleAcademicpeer-review


The application of hexa[(dimethylamino)methyl]-functionalized triphenylphosphine (1) and its benzylammonium salt, Bn-Dendriphos (2), in the Suzuki-Miyaura cross-coupling of aryl bromides with arylboronic acids is described. The 3,5-bis[(benzyldimethylammonio)methyl] substitution pattern in 2 leads to a rate enhancement compared to both the non-ionic parent compound 1 and triphenylphospine (PPh3) itself. At the same time, the resulting catalytic species are stable towards palladium black formation, even at a phosphine/palladium ratio of 1. These observations are attributed to the presence of a total of six ammonium groups in the backbone of the phosphine ligand, which presumably leads to an unsaturated phosphine-palladium complex.
Original languageUndefined/Unknown
Pages (from-to)262-266
Number of pages5
JournalAdvanced synthesis & catalysis
Issue number2
Publication statusPublished - 2008

Cite this