Review on green chemistry — Suzuki cross coupling in aqueous media

Abstract

The Suzuki cross-coupling reaction is a very efficient, reliable, and environmentally friendly method for the introduction of novel carbon–carbon bonds into molecules. This review summarizes recent advances in the use of the reaction in aqueous media with a focus on different types of ligands and the ligandless protocols currently in use. Several synthetic targets for the reaction have been mentioned. The work summarizes recent results from studies on asymmetric Suzuki reactions performed in organic – aqueous mixed solvents.Key words: Suzuki reaction, green chemistry, metal-catalyzed cross-coupling reactions, aqueous synthesis media.

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

“…[61] Our working hypothesis is that basic nitrogen atoms in pyridines, indoles or primary amines prefer to engage in hydrogen-bonding interactions with water rather than to inhibit the catalytically active metal centre. Apart from being a cheap, safe and benign solvent, [62][63][64] water has the additional advantage that the organic products of the coupling reactions are often poorly soluble and can thus easily be separated from the reaction mixture. This advantage, though, also turns out to be a drawback, as the aryl halide reactants tend to be poorly soluble in water, leading Abstract: A dicyclohexyl(2-sulfo-9-(3-(4-sulfophenyl)propyl)-9H-fluoren-9-yl)phosphonium salt was synthesized in 64 % overall yield in three steps from simple commercially available starting materials.…”

One step synthesis of Diflunisal using a Pd-diamine complex

“…Phosphine-based complexes catalyzed the reaction but in ethanol Diflunisal was achieved only in moderate to good yields (Table 1, entries 1 and 3). Giordano et al have used another commonly used phosphine catalyst, Pd(PPh 3 ) 4 , and achieved 70% in Suzuki reaction in ethanol (Scheme 4) [19].…”

“…Giordano et al prepared Diflunisal in two steps starting with preparation of a phenylboronic acid from the corresponding Grignard reagent in 84.3% yield (2,4-difluorophenylboronic acid is also commercially available at present time) and continued through the Suzuki reaction. Phosphine based Pd(PPh 3 ) 4 was required in this successful reaction sequence, achieving Diflunisal in 59% total yield (Scheme 4) [19].…”

“…The biaryl moiety interacts favorably with polar groups such as amides and hydroxyl groups. Because of these unique physicochemical properties it has become a privileged substructure in pharmaceuticals [1,2] The biaryl moiety is present in drugs like Diflunisal 1, Felbinac 2, Flurbiprofen, Fenbufen and Xenbucin [3][4][5]. Also many larger molecules, for example natural cyclic peptide antibiotics including the Biphenomycins A-C [6], anti-HIV agents Chloropeptin I and II [7] and Sartan-type drugs (for example Irbesartan for the treatment of arterial hypertension [8]), contain a biaryl moiety (Fig.…”

Organometall‐Reaktionen in Wasser

“…Um Suzuki-Reaktionen in wässrigen Systemen durchführen zu können [28,29], ist es von Vorteil, den Katalysator in eine wasserlösliche Form zu überführen. Es bietet sich an, hierfür den Liganden zu modifizieren und mit hydrophilen funktionellen Gruppen auszustatten.…”