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On the direct use of CO 2 in multicomponent reactions: introducing the Passerini four component reaction
- Source :
- RSC Advances, RSC Advances, Royal Society of Chemistry, 2018, 8 (55), pp.31490-31495. ⟨10.1039/c8ra07150k⟩
- Publication Year :
- 2018
-
Abstract
- International audience; 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.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
General Chemical Engineering
Carboxylic acid
Isocyanide
Butanol
Multicomponent
Alcohol
General Chemistry
Passerini
010402 general chemistry
01 natural sciences
Aldehyde
0104 chemical sciences
Catalysis
Solvent
chemistry.chemical_compound
Organic chemistry
CO2
Isobutyraldehyde
Subjects
Details
- ISSN :
- 20462069
- Database :
- OpenAIRE
- Journal :
- RSC Advances
- Accession number :
- edsair.doi.dedup.....0ea82bb01d2078549f8f9efe39259eca
- Full Text :
- https://doi.org/10.1039/c8ra07150k