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A more sustainable and highly practicable synthesis of aliphatic isocyanides

Waibel, K. A.; Nickisch, R.; Möhl, N.; Seim, R.; Meier, M. A. R.

Abstract:
Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.

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Verlagsausgabe §
DOI: 10.5445/IR/1000117605
Veröffentlicht am 09.03.2020
Originalveröffentlichung
DOI: 10.1039/C9GC04070F
Scopus
Zitationen: 6
Web of Science
Zitationen: 5
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 1463-9262, 1463-9270
KITopen-ID: 1000117605
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Green chemistry
Verlag Royal Society of Chemistry (RSC)
Band 22
Heft 3
Seiten 933–941
Vorab online veröffentlicht am 16.01.2020
Nachgewiesen in Scopus
Web of Science
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