ONWUKAMIKE, Kelechukwu Nnabuike; GRELIER, Stéphane; GRAU, Etienne; CRAMAIL, Henri; MEIER, Michael

doi:10.1039/c8ra07150k

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ONWUKAMIKE, Kelechukwu Nnabuike
Laboratoire de Chimie des Polymères Organiques [LCPO]

GRELIER, Stéphane
Laboratoire de Chimie des Polymères Organiques [LCPO]

GRAU, Etienne

Laboratoire de Chimie des Polymères Organiques [LCPO]

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RSC Advances. 2018, vol. 8, n° 55, p. 31490-31495

Royal Society of Chemistry

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We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO 2. Key to this approach is the use of a switchable solvent system, allowing the synthesis of a variety of a-carbonate-amides. The reaction was first investigated and optimized using butanol, isobutyraldehyde, tert-butyl isocyanide and CO 2. Parameters investigated included the effect of reactant equivalents, reactant concentration, solvent, catalyst, catalyst concentration and CO 2 pressure. Of the other parameters, the purity of the aldehyde and its tendency to oxidize was one of the most critical parameters for a successful P-4CR. After optimization, a total of twelve (12) P-4CR compounds were synthesized with conversions ranging between 16 and 82% and isolated yields between 18 and 43%. Their structures were confirmed via 1 H and 13 C NMR, FT-IR and high resolution mass spectrometry (ESI-MS). In addition, three (3) hydrolysis products of P-4CR (a-hydroxyl-amides) were successfully isolated with yields between 23 and 63% and fully characterized (1 H, 13 C NMR, FT-IR and ESI-MS) as well.< Réduire

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Multicomponent

CO2

Passerini

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On the direct use of CO 2 in multicomponent reactions: introducing the Passerini four component reaction

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