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

Hervé, Gwénaëlle; Len, Christophe

doi:10.1186/s40508-015-0029-2

Cited by 30 publications

(11 citation statements)

References 31 publications

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“…Palladium complex 133 and a complex of ligand 134 (Figure 18) are used for catalysing the Heck reaction successfully in water. A review by Hervé and Len [65] is based on both Heck and Sonogashira cross-coupling of nucleosides following two important aspects of the green chemistry, i.e., use of aqueous medium and no protection/deprotection steps. It focuses on the study of C5-modified pyrimidines and C7-deaza or C8-modified purines where these chemical modifications have been developed using palladium cross-coupling reactions.…”

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confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

175

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

175

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“…Therefore, we investigated the Sonogashira coupling of 5-IdC with substituted alkynes and the resultant outcome was promising showing our ability to perform Cu-free Sonogashira in 45 min (Scheme 9). The short reaction time and low catalyst loading sets this protocol apart from other conventional Sonogashira reactions [57]. Sonogashira cross-coupling of 5-IdU with an alkyne derivative was found to be highly efficient followed by in situ cyclization to furnish the bicyclic product.…”

Section: Sonogashira Cross-coupling Using Pd/ptabsmentioning

confidence: 99%

Section: Sonogashira Cross-coupling Using Pd/ptabsmentioning

confidence: 99%

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Bhilare

Shet

Sanghvi³

et al. 2020

Molecules

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Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of interest toward conducting useful biochemical, pharmaceutical, and mutagenic study. For accessing such synthetically useful structures and features, transition-metal catalyzed processes have been proven over the years to be an excellent tool for carrying out the various transformations with ease and under mild reaction conditions. Amidst various transition-metal catalyzed processes available for nucleoside modification, Pd-catalyzed cross-coupling reactions have proven to be perhaps the most efficient, successful, and broadly applicable reactions in both academia and industry. Pd-catalyzed C–C and C–heteroatom bond forming reactions have been widely used for the modification of the heterocyclic moiety in the nucleosides, although a single catalyst system that could address all the different requirements for nucleoside modifications isvery rare or non-existent. With this in mind, we present herein a review showcasing the recent developments and improvements from our research groups toward the development of Pd-catalyzed strategies including drug synthesis using a single efficient catalyst system for the modification of nucleosides and other heterocycles. The review also highlights the improvement in conditions or the yield of various bio-active nucleosides or commercial drugs possessing the nucleoside structural core. Scale ups wherever performed (up to 100 g) of molecules of commercial importance have also been disclosed.

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“…The addition of copper salts in catalytic amounts as co‐catalysts (or sometimes in stoichiometric amounts) to promote general Sonogashira coupling reactions (by the formation of copper‐acetylide) results in lower yields of the alkyne‐functionalized nucleosides. One of the reasons for the reduced yields would be the ability of Cu to bind strongly with the nucleoside structural backbone or promote side reactions [28] …”

Section: Derivatization Of Pta and Applications In Catalysismentioning

confidence: 99%

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes

Bandaru

Bhilare

Schulzke

et al. 2020

The Chemical Record

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Phosphines have, in combination with transition metals, played a pivotal role in the rapid development of efficient catalytic processes. Caged phosphines constitute a class of three‐dimensional scaffolds providing unique control over steric and electronic properties. The versatility of the caged phosphine ligands has been demonstrated elegantly by the groups of Verkade, Gonzalvi as well as Stradiotto. Our research group has also been working extensively for the past several years in the development of 1,3,5‐triaza‐7‐phosphaadamantane‐based caged ligands and in this personal note we have summarized these applications pertaining to the modification of biologically useful nucleosides and heteroarenes.

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

Cited by 30 publications

References 31 publications

Heck Reaction—State of the Art

Heck Reaction—State of the Art

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes

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