On the direct use of CO 2 in multicomponent reactions: introducing the Passerini four component reaction
| dc.rights.license | open | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Karlsruher Institut für Technologie [KIT] | |
| dc.contributor.author | ONWUKAMIKE, Kelechukwu Nnabuike | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | GRELIER, Stéphane | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | GRAU, Etienne
IDREF: 187909261 | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | CRAMAIL, Henri | |
| hal.structure.identifier | Karlsruher Institut für Technologie [KIT] | |
| dc.contributor.author | MEIER, Michael | |
| dc.date.accessioned | 2020 | |
| dc.date.available | 2020 | |
| dc.date.issued | 2018 | |
| dc.identifier.issn | 2046-2069 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/19811 | |
| dc.description.abstractEn | 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. | |
| dc.language.iso | en | |
| dc.publisher | Royal Society of Chemistry | |
| dc.subject.en | Multicomponent | |
| dc.subject.en | CO2 | |
| dc.subject.en | Passerini | |
| dc.title.en | On the direct use of CO 2 in multicomponent reactions: introducing the Passerini four component reaction | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1039/c8ra07150k | |
| dc.subject.hal | Chimie/Chimie organique | |
| bordeaux.journal | RSC Advances | |
| bordeaux.page | 31490-31495 | |
| bordeaux.volume | 8 | |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | * |
| bordeaux.issue | 55 | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.peerReviewed | oui | |
| hal.identifier | hal-01972921 | |
| hal.version | 1 | |
| hal.origin.link | https://hal.archives-ouvertes.fr//hal-01972921v1 | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=RSC%20Advances&rft.date=2018&rft.volume=8&rft.issue=55&rft.spage=31490-31495&rft.epage=31490-31495&rft.eissn=2046-2069&rft.issn=2046-2069&rft.au=ONWUKAMIKE,%20Kelechukwu%20Nnabuike&GRELIER,%20St%C3%A9phane&GRAU,%20Etienne&CRAMAIL,%20Henri&MEIER,%20Michael&rft.genre=article |
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