Alternative synthesis of alverine

Shakhmaev, R. N.; Сунагатуллина, А. Ш.; Зорин, В. В.

doi:10.1134/s1070428017060045

Cited by 11 publications

(8 citation statements)

References 18 publications

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“…In this regard, recent studies by Shakhmaev and co‐workers demonstrated the effect of substoichiometric amounts of NMP on C(sp 2 )−C(sp 2 ) allyl–aryl cross‐couplings using Fe(acac) 3 (1 mol %; Scheme ) . This method was applied to short syntheses of allylamine pharmaceuticals, such as naftifine (antifungal), cinnarizine (antihistamine), and flunarizine (calcium antagonist) . It is likely that the amino group of the substrate acts as a ligand to iron in these couplings …”

Section: Development Of Sustainable Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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The scarcity of precious metals has led to the development of sustainable strategies for metal-catalyzed cross-coupling reactions. The establishment of new catalytic methods using iron is attractive owing to the low cost, abundance, ready availability, and very low toxicity of iron. In the last few years, sustainable methods for iron-catalyzed cross-couplings have entered the critical area of pharmaceutical research. Most notably, iron is one of the very few metals that have been successfully field-tested as highly effective base-metal catalysts in practical, kilogram-scale industrial cross-couplings. In this Minireview, we critically discuss the strategic benefits of using iron catalysts as green and sustainable alternatives to precious metals in cross-coupling applications for the synthesis of pharmaceuticals. The Minireview provides an essential introduction to the fundamental aspects of practical iron catalysis, highlights areas for improvement, and identifies new fields to be explored.

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Section: Development Of Sustainable Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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“…25 Another amine-containing molecule, naine, an antifungal drug, was prepared by an iron-catalysed coupling of a (E)-chloroolen 15 and phenyl Grignard reagent in high yield (89%) and excellent stereoselectivity (Scheme 6). 26 Vinyl (pseudo)halides. However greatest applications with vinyl electrophiles in total synthesis have been found with vinyl triates, as established by Fürstner.…”

Section: Cross-coupling Reactions Of Organometallic Reagentsmentioning

confidence: 99%

Iron-promoted C–C bond formation in the total synthesis of natural products and drugs

Legros

Figadère

2015

Nat. Prod. Rep.

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“…Finally, to highlight the practical value of this method, we have demonstrated a short synthesis of naftifine, a best‐selling antifungal drug (Scheme ) . The use of a benign ligand N ‐methylcaprolactam presents a key advantage from the environmental and operational standpoints …”

Section: Figurementioning

confidence: 99%

N‐Methylcaprolactam as a Dipolar Aprotic Solvent for Iron‐Catalyzed Cross‐Coupling Reactions: Matching Efficiency with Safer Reaction Media

2019

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Although iron‐catalysis provides a powerful alternative to the more conventional palladium and nickel in the cross‐coupling arena, the major limitation is the necessity for carcinogenic N‐methylpyrrolidone as a co‐solvent in the vast majority of catalytic reactions. Herein, we introduce N‐methylcaprolactam as an efficient, non‐toxic and practical dipolar aprotic solvent for iron‐catalyzed C(sp2)−C(sp3) alkylative cross‐coupling of aryl chlorides and tosylates. The utility of this method is reflected by its wide substrate scope, high yields and capacity to cross‐couple challenging alkyl organometallics prone to b‐hydride elimination and homocoupling. Considering the broad utility of iron‐catalyzed cross‐coupling, we envision that N‐methylcaprolactam will find wide application as a substitute for carcinogenic NMP.

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Alternative synthesis of alverine

Cited by 11 publications

References 18 publications

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Iron-promoted C–C bond formation in the total synthesis of natural products and drugs

N‐Methylcaprolactam as a Dipolar Aprotic Solvent for Iron‐Catalyzed Cross‐Coupling Reactions: Matching Efficiency with Safer Reaction Media

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