Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 6, Issue 11, Pages 14063-14070Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b02614
Keywords
Imidazolium salt; Allylic substitution; Metal-free; Allylic anilines; Sustainable
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Funding
- University of Alicante [VIGROB-285]
- Spanish Ministerio de Economia y Competitividad [CTQ2015-66624-P]
- Spanish Ministerio de Education, Cultura y Deporte [FPUIS/06040]
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The 1,3-bis(carboxymethyl)imidazolium chloride, which is easily and in a straightforward manner prepared readily from starting materials in multigram scale, is employed as catalyst in the synthesis of N-allylanilines by allylic substitution of alcohols with anilines. This metal-free catalyst allows the reaction to be carried out under mild reaction conditions (80 degrees C and air open vessel) and proved to be efficient for a diversity of anilines and allylic alcohols, providing exclusively the product of N-substitution independently of the substituents in the aniline reactant. The process described is simple and effective, allowing N-allylanilines to be obtained in preparative scale [e.g., 3.30 g of N-(1,3diphenylallyl)-4-nitroaniline]. The catalyst could be reused up to 15 cycles without loss of activity, proving its robustness.
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