1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst

The synthesis of a task‐specific ionic liquid (TSIL) based on a BMIM ionic liquid phosphane is achieved by modification of the original procedure. It is used as a ligand with AgOAc, and the resulting complex is fully characterized. This catalytic system promotes the 1,3‐dipolar cycloaddition of stab...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-07, Vol.2019 (25), p.4095-4100
Main Authors: Lledó, David, Grindlay, Guillermo, Sansano, José Miguel
Format: Article
Language:English
Subjects:
Alkenes
Catalysis
Chemical synthesis
Cycloaddition
Green chemistry
Ionic liquids
Ions
Silver
Ylides
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Summary:The synthesis of a task‐specific ionic liquid (TSIL) based on a BMIM ionic liquid phosphane is achieved by modification of the original procedure. It is used as a ligand with AgOAc, and the resulting complex is fully characterized. This catalytic system promotes the 1,3‐dipolar cycloaddition of stabilized azomethine ylides and electrophilic alkenes using a green methodology. The green character was analyzed using an overall set of parameters finding the optimal conditions and individualized separation/purification methods for each cycloadduct. The determination of the most important green metrics is reported in this survey, demonstrating the value of this methodology on a laboratory scale or even at an industrial level. An environmentally friendly 1,3‐dipolar cycloaddition between imino esters and electrophilic alkenes with excellent green metrics was developed using a versatile, efficient, stable and fully recoverable TSIL·AgOAc catalyst.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900724