Suzuki cross-coupling in aqueous media catalyzed by a 1,1′-N-substituted ferrocenediyl Pd(II) complex

Weng, Zhiqiang; Koh, Lip Lin; Hor, T. S. Andy

doi:10.1016/j.jorganchem.2003.09.028

Cited by 39 publications

(12 citation statements)

References 25 publications

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“…The structure of 18 (Fig. 6) is very similar to that of its dichloro analogue (1,1 0 -bis(benzylideneamino)ferrocene-N,N 0 )-dichloro-palladium(II) [27], the principal difference being in the inclination of the phenyl rings to their associated cyclopentadienyl rings. In 18 the C(2)-C(6) ring is inclined by ca.…”

Section: Reaction Of 10-12 With Titanium Precursorsmentioning

confidence: 80%

The synthesis, coordination chemistry and ethylene polymerisation activity of ferrocenediyl nitrogen-substituted ligands and their metal complexes

Gibson

Gregson

Halliwell

et al. 2005

Journal of Organometallic Chemistry

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Section: Reaction Of 10-12 With Titanium Precursorsmentioning

confidence: 80%

The synthesis, coordination chemistry and ethylene polymerisation activity of ferrocenediyl nitrogen-substituted ligands and their metal complexes

Gibson

Gregson

Halliwell

et al. 2005

Journal of Organometallic Chemistry

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“…[25,27,[38][39][40] However, yields of Ͻ35 % of aryl-aryl coupling products seem to be quite typical. [25,27,[38][39][40] However, yields of Ͻ35 % of aryl-aryl coupling products seem to be quite typical.…”

Section: Resultsmentioning

confidence: 99%

“…[25,27,[38][39][40] However, yields of Ͻ35 % of aryl-aryl coupling products seem to be quite typical. [39] In comparison, good results (62 % yield) were obtained in the reaction of 4-chlorotoluene and benzeneboronic acid in pure water by using microwaves instead of conventional heating. [38] The use of a 1,1Ј-N-substituted ferrocenediyl-Pd II complex did not catalyze the coupling of 4-CNC 6 H 4 Cl although this ligand was active in the coupling of aryl bromides.…”

Section: Resultsmentioning

confidence: 99%

The Suzuki Coupling of Aryl Chlorides in Aqueous Media Catalyzed by in situ Generated Calix[4]arene‐Based N‐Heterocyclic Carbene Ligands

2006

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We report on the use of an in situ system for the catalytic Suzuki cross‐coupling reaction of chlorobenzenes and benzeneboronic acid to yield biphenyls. Calix[4]arene‐based imidazolium salts were used as precursors of N‐heterocyclic carbene ligands and Pd(OAc)2 as the palladium source. In dioxane as the organic medium, the steric demands of the substituents on the calixarene skeleton and on the imidazolium moiety parallel the catalytic activity; the best catalytic results were obtained by using dimesityl‐ or 2,6‐diisopropylphenyl‐substituted calixarene‐imidazolium salts. Among the bases tested Cs2CO3 and CsF were the most effective. The catalytic protocol established for organic solvents could also be used for the Suzuki cross‐coupling reaction in aqueous solution. In dioxane/water (50:50) the activity is nearly the same as in pure dioxane and in pure water, an environmentally friendly and cheap solvent, a 60 % level of reactivity was maintained; here the calixarene ligand precursor 3a showed the highest activity. Nonmacrocyclic compounds used for comparison showed considerably lower catalytic ability proving that calix[4]arene‐based imidazolium salts are attractive supramolecular skeletons for the N‐heterocyclic carbene ligands used in selective Suzuki cross‐coupling reactions of aryl chlorides in aqueous solution. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…Aqueous-phase Suzuki couplings of activated aryl bromides catalyzed by complex 5 gave good yields of biphenyl products (eq 11) [82]. Yields with 4-bromoanisole were somewhat lower (51-67%), however.…”

Section: Meo2 C Co2mementioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Shaughnessy¹,

DeVasher²

2005

COC

181

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Water has attracted significant attention as an alternative solvent for homogeneous metal-catalyzed reactions because it is a non-toxic, nonflammable solvent that can allow for simplified recovery of homogeneous catalysts. The use of water as a solvent in palladium-catalyzed cross-coupling reactions is of great academic and industrial interest. Palladium-catalyzed coupling reactions are powerful methods to make carbon-carbon and carbon-heteroatom bonds under mild conditions. Separation of the catalyst from the organic product can be very difficult; however, constraining the catalyst to the aqueous-phase of an aqueous-biphasic solvent system can potentially simplify catalyst recovery. This review will focus on recent developments in the design and application of aqueous-phase, palladium-catalyzed coupling reactions over the period from 2000, through late 2004. A variety of new hydrophilic ligand architectures have been introduced recently that provide significantly more active catalysts towards industrially relevant aryl bromides and chlorides. Stille CouplingRSiX3 L n Pd(Cat) Hiyama Coupling

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Suzuki cross-coupling in aqueous media catalyzed by a 1,1′-N-substituted ferrocenediyl Pd(II) complex

Cited by 39 publications

References 25 publications

The synthesis, coordination chemistry and ethylene polymerisation activity of ferrocenediyl nitrogen-substituted ligands and their metal complexes

The synthesis, coordination chemistry and ethylene polymerisation activity of ferrocenediyl nitrogen-substituted ligands and their metal complexes

The Suzuki Coupling of Aryl Chlorides in Aqueous Media Catalyzed by in situ Generated Calix[4]arene‐Based N‐Heterocyclic Carbene Ligands

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

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