Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 2, Pages 262-266Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700366
Keywords
C-C coupling; Dendriphos; palladium; phosphine; Suzuki-Miyaura reaction
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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.
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