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On the direct use of CO2 in multicomponent reactions: Introducing the Passerini four component reaction

Onwukamike, Kelechukwu Nnabuike; Grelier, S.; Grau, E.; Cramail, H.; Meier, Michael A. R.

Abstract:
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 CO2. Key to this approach is the use of a switchable solvent system, allowing the synthesis of a variety of α-carbonate-amides. The reaction was first investigated and optimized using butanol, isobutyraldehyde, tert-butyl isocyanide and CO2. Parameters investigated included the effect of reactant equivalents, reactant concentration, solvent, catalyst, catalyst concentration and CO2 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 1H and 13C NMR, FT-IR and high resolution mass spectrometry (ESI-MS). In addition, three (3) hydrolysis products of P-4CR (α-hydroxyl-amides) were successfully isolated with yields between 23 and 63% and fully characterized (1H, 13C NMR, FT-IR and ESI-MS) as well.

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Verlagsausgabe §
DOI: 10.5445/IR/1000086252
Veröffentlicht am 05.10.2018
Originalveröffentlichung
DOI: 10.1039/c8ra07150k
Scopus
Zitationen: 1
Web of Science
Zitationen: 1
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2018
Sprache Englisch
Identifikator ISSN: 2046-2069
urn:nbn:de:swb:90-862522
KITopen-ID: 1000086252
Erschienen in RSC Advances
Verlag Royal Society of Chemistry (RSC)
Band 8
Heft 55
Seiten 31490-31495
Nachgewiesen in Web of Science
Scopus
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