Palladium Suzuki-Miyaura cross-coupling

Scheme 10. Proposed mechanistic cycle for Suzuki-Miyaura cross-coupling based on tbe observation of binuclear palladium complexes. L=l.l -(cyclohexylpbospbanediyl)dipiperidine.

Figure 3.63). The palladium(II) complex was used in the Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and benzyl bromide, 2-bromo and 4-bromo benzalde-hyde, respectively [180-182],...

Grasa, G. A., Viciu, M. S., Huang, J., Zhang, C., Trudell, M. L., Nolan, S. P. Suzuki-Miyaura Cross-Coupling Reactions Mediated by Palladium/lmidazolium Salt Systems. Organometallics 2002, 21,2866-2873. 

A convenient and effective palladium-catalysed Suzuki-Miyaura cross coupling reaction of deactivated aryl chlorides with phenylboronic acid utilised the 1,3-diazepinium salts 107 as in situ precursors of the palladium ligands. These salts were prepared from the diamines 106 and cyclocondensation with triethyl orthoformate <05SL2394>. 

Martin R, Buchwald SL (2008) Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. Acc Chem Res 41 1461-1473... 

Arylation of ketones, aryl amination and suzuki-miyaura cross coupling using a well-defined palladium catalyst bearing an w-heterocyclic carbene ligand... 

ARYLATION OF KETONES, ARYL AMINATION AND SUZUKI-MIYAURA CROSS COUPLING USING A WELL-DEFINED PALLADIUM CATALYST BEARING AN /V-HETEROCYCLIC CARBENE LIGAND... 

The Suzuki-Miyaura cross-coupling reaction is a standard method for carbon-carbon bond formation between an aryl halide or triflate and a boronic acid derivative, catalyzed by a palladium-metal complex. As with the Mizoroki-Heck reaction, this cross-coupling reaction has been developed in ionic liquids in order to recycle and reuse the catalyst. In 2000, the first cross-coupling of a halide derivative with phenylboronic acid in [bmim] [BF4] was described. As expected, the reaction proceeded much faster with bromobenzene and iodobenzene, whereas almost no biphenyl 91 was obtained using the chloride derivative (Scheme 36). The ionic liquid allowed the reactivity to be increased, with a turnover number between 72 and 78. Furthermore, the catalyst could be reused repeatedly without loss of activity, even when the reaction was performed under air. Cross-coupling with chlorobenzene was later achieved - although with only a moderate yield (42%) - using ultrasound activation. 

Yamada YMA, Watanabe T, Torii K et al (2010) Palladium membrane-installed microchannel devices for instantaneous Suzuki-Miyaura cross-coupling. Chem Eur J 16 11311-11319... 

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