Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water:  Scope and Limitations

Badone, Domenico; Baroni, Marco Giorgio; Cardamone, Rosanna; Ielmini, and A.; Guzzi, U.

doi:10.1021/jo970439i

Cited by 276 publications

(121 citation statements)

References 33 publications

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“…This reaction was carried out in accordance with Badone's observation that tetrabutylammonium bromide accelerates the rate of the SM cross-coupling in water without the use of an organic solvent. 89 Kirsch and Hesse 90 have used the mild procedure to couple b-chloroacroleins with a wide variety of boronic acids to prepare tetrasubstituted alkenes (Scheme 38). Although aryl chlorides are less reactive due to their inert nature in the oxidative addition step, the SM cross-coupling of vinyl chloride is easier when compared to the aryl and alkyl chlorides.…”

Section: Sm Cross-coupling Reactions Under Green Conditionsmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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Section: Sm Cross-coupling Reactions Under Green Conditionsmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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“…However, in the case of Diflunisal synthesis, the reaction proceeded in low yield ( Although the reactions had to be performed at higher temperatures, the advantage was to obtain the products in higher purity. Finally, we added TBAB to the reaction mixture to form a boronate complex ArB(OH) 3 -Bu 4 N + which has been thought to play an active role in the transmetallation step [50][51][52]. Unfortunately with DMF as the solvent, we could not significantly improve the yields for the preparation of Diflunisal by adding TBAB to the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

One step synthesis of Diflunisal using a Pd-diamine complex

Kylmälä

Tois

et al. 2009

Open Chemistry

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Diflunisal and Felbinac , two FDA-approved NSAIDs and other biphenyl carboxylic acids were prepared in one step by a simple and clean Suzuki cross-coupling reaction using an easily synthesized, air and moisture stable, palladium-diamine complex. The yield (93%) for the one-step preparation of Diflunisal is the best reported without using a glovebox and a phoshine-based catalyst.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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“…22 Recently described microwave assisted intramolecular reaction of this type, carried out under PTC conditions with catalytic amount of TAA salt, seems to be very promising. 23 Of great importance are hydrogenation and reduction reactions, mediated by PT catalysts and metal carbonyls or complexes.…”

Section: Phmentioning

confidence: 99%

Co-catalysis in phase transfer catalyzed reactions (a concept paper)

Mąkosza¹,

Fedoryński²

2006

Arkivoc

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In this short paper the concept of co-catalysis in phase transfer catalyzed reactions is presented. It was shown that difficulties in the application of phase transfer catalysis for reactions of nonlipophilic inorganic anions such as hydroxide and fluoride anions can be efficiently eliminated when carried out in the presence of co-catalysts.On selected examples it was shown that numerous processes catalyzed by transition metals are substantially improved when carried out in the two-phase systems in the presence of phase transfer catalysts. Modus operandi of such co-catalytic systems varied depending on the kind of transition metal catalyzed process.Keywords: Phase-transfer catalysis, tetraalkyl ammonium salts, β-elimination, carbonylation, fluorination, Heck reaction, Suzuki reaction Phase-transfer catalysis (PTC) is presently a well established, general methodology widely used in laboratory synthesis and chemical industry. The main feature of this methodology is that reactions are carried out in two-phase systems containing organic and aqueous phases of negligible mutual solubility whereas the catalytic process consists in continuous introduction of reacting anionic species into nonpolar organic phase in form of ion pairs with lipophilic cations supplied by the catalyst. Typical PT catalysts are lipophilic tetraalkylammonium (TAA) salts. Further reactions of these species e.g. with appropriate electrophilic partners proceed in the organic phase. 1,2 There are two general systems in which PT catalyzed reactions are carried out: liquidliquid and liquid-solid, and two major cases: the reacting anionic species are available before the (1)The key factor deciding on feasibility of the catalytic process is the position of the ionexchange equilibrium 1a that governs the concentration of the reacting anions in the organic phase. This equilibrium is in turn governed by the energy of hydration of the anions X -and Y -.In the row OH -, SO 4 2-, F -, Cl -, CN -, Br -, I -, ClO 4 -, SCN -etc. always right partner will be preferentially located in the organic phase. Thus a substantial limitation of the PTC is that hydroxide and fluoride anions cannot be efficiently transferred into the organic phase when other, more lipophilic, anions are present in the system. Co-catalysis.Many catalysts exhibit the desired action or act more efficiently only in the presence of an additional component. Such additional components that make the catalytic process possible, activate the catalyst or modify its action are known as co-catalysts. Co-catalytic processes are widely used in laboratory practice and industrial applications. This phenomenon is frequently observed in the nature, many natural catalysts -enzymes require cocatalystscoenzymes -for proper action. The phenomenon of cocatalysis in PT catalyzed reactions can be of various nature. The first category of PTC cocatalysis is applicable for reactions of hydrophilic anions, that due to unfavourable ion exchange equilibrium cannot operate efficiently in simple PT catalyzed syst...

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Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water: Scope and Limitations

Cited by 276 publications

References 33 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

One step synthesis of Diflunisal using a Pd-diamine complex

Co-catalysis in phase transfer catalyzed reactions (a concept paper)

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