A More Sustainable Isocyanide Synthesis from N-Substituted Formamides Using Phosphorus Oxychloride in the Presence of Triethylamine as Solvent

A simple, green, and highly efficient protocol for the synthesis of isocyanides is described. The reaction involves dehydration of formamides with phosphorus oxychloride in the presence of triethylamine as solvent at 0 °C. The product isocyanides were obtained in high to excellent yields in less tha...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 27; no. 20; p. 6850
Main Authors Salami, Sodeeq Aderotimi, Siwe-Noundou, Xavier, Krause, Rui Werner Maçedo
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 13.10.2022
MDPI
Subjects
Chemists
Chloride
Dehydration
Green chemistry
Iodine
isocyanides
Laboratories
N-substituted formamides
Organic chemicals
Phosphorus
phosphorus oxychloride
Reagents
Solvents
Triethylamine
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Summary:A simple, green, and highly efficient protocol for the synthesis of isocyanides is described. The reaction involves dehydration of formamides with phosphorus oxychloride in the presence of triethylamine as solvent at 0 °C. The product isocyanides were obtained in high to excellent yields in less than 5 min. The method offers several advantages including increased synthesis speed, relatively mild conditions, and rapid access to large numbers of functionalized isocyanides, excellent purity, increased safety, and minimal reaction waste. The new approach of synthesising dehydrative isocyanides from formamides is significantly more environmentally-friendly than prior methods.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27206850