Palladium-catalyzed Suzuki reaction in aqueous solvents applied to unprotected nucleosides and nucleotides

Hervé, Gwénaëlle; Sartori, Guillaume; Enderlin, Gérald; Mackenzie, Grahame; Len, Christophe

doi:10.1039/c3ra47911k

Cited by 77 publications

(30 citation statements)

References 86 publications

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“…The presence of the chlorine or of the oxygen atoms did not seem to change the lipophilic properties of the reactant. Consequently compounds 45, 46 and 47 were isolated in the same range of yields (Table 4, entries [6][7][8]. In order to modulate the structure, substitution (M = Na + , K + ) (10 to 20 mol%) in presence of CuI (0.2 eq to 0.5 eq) and NEt 3 (2 eq to 10 eq).…”

Section: Pd(ii)-catalyzed Heck Cross-coupling In H 2 Omentioning

confidence: 99%

“…In order to use safer solvents and auxiliaries, to limit the risks and hazards, different groups have reported recently those cross-couplings in greener solvents such as water without the need for protection and deprotection steps. Since recent developments and a complete review on Suzuki-Miyaura reaction applied to unprotected nucleosides were reported by our group [7,[12][13][14][15], this paper will focused on the Heck reactions and Sonogashira reactions applied to unprotected nucleosides and nucleotides in aqueous media or water as sole solvent. For the sake of clarity, this review has been arranged to describe the Heck reaction and then the Sonogashira reaction.…”

mentioning

confidence: 99%

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Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Hervé

Len

2015

Sustain Chem Process

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Amongst all synthetic nucleosides having high potential biological activities, C5-modified pyrimidines and C7-deaza or C8-modified purines have been particularly studied. These main chemical modifications have been developed using palladium cross-coupling reactions. This review focus on both Heck and Sonogashira cross-coupling of nucleosides using different aspects of the twelve principles of green chemistry: use of aqueous medium and no protection/deprotection steps.

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Section: Pd(ii)-catalyzed Heck Cross-coupling In H 2 Omentioning

confidence: 99%

mentioning

confidence: 99%

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Hervé

Len

2015

Sustain Chem Process

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“…Compared to related C-C bond formations, the environmentally benign nature, high functional group tolerance, wide commercial availability of the reactants, and compatibility with aqueous conditions are advantageous [10][11][12]. As a result, various research groups have utilized and reviewed this reaction for the derivatization of complex molecules such as natural products [13][14][15][16] and nucleosides [17][18][19][20][21][22][23]. The mechanism of this reaction originally proposed by Miyaura and Suzuki has been revisited recently, which provides insights useful for rational reaction optimization [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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Abstract:The (site-selective) derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure-activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in (partial) aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis (SPPS) or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki-Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable.

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“…In the context of green chemistry, catalysis and alternative media, different cross-coupling reactions such as Suzuki-Miyaura in batch reactors have been developed in aqueous media or in water as sole green safer solvent via conventional heating or microwave irradiation [32][33][34][35][36][37][38][39][40][41][42][43]. Continuous flow chemistry as alternative technology offers significant processing advantages including improved thermal management, mixing control, application to a wider range of reaction conditions, scalability, energy efficiency, waste reduction, safety, use of heterogeneous catalysis, multistep synthesis and much more [44][45][46][47][48][49].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling in Continuous Flow

et al. 2017

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Carbon-carbon cross-coupling reactions are among the most important processes in organic chemistry and Suzuki-Miyaura reactions are the most widely used protocols. For a decade, green chemistry and particularly catalysis and continuous flow, have shown immense potential in achieving the goals of "greener synthesis". To date, it seems difficult to conceive the chemistry of the 21st century without the industrialization of continuous flow process in the area of pharmaceuticals, drugs, agrochemicals, polymers, etc. A large variety of palladium Suzuki-Miyaura cross-coupling reactions have been developed using a continuous flow sequence for preparing the desired biaryl derivatives. Our objective is to focus this review on the continuous flow Suzuki-Miyaura cross-coupling using homogeneous and heterogeneous catalysts.

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Palladium-catalyzed Suzuki reaction in aqueous solvents applied to unprotected nucleosides and nucleotides

Abstract: Nucleoside analogues have attracted much attention due to their potential biological activities.

Cited by 77 publications

References 86 publications

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling in Continuous Flow

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