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

Abstract

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.

n-selective Tsuji–Trost allylation promoted by a recyclable TSIL-palladium complex

“…The TSIL ligand 1, prepared according to Scheme 1, was successfully employed as ligand in silver(I)promoted 1,3-dipolar cycloadditions [32] and also in the palladium(II)-catalyzed Suzuki-Miyaura coupling in water [33].…”

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition

“…For the reasons mentioned above, 1,3-DCR has been described as "the single most important method for the construction of heterocyclic five-membered rings" (Jørgensen, 2002;Gupta and Khurana., 2019;Thadem et al, 2021). Major hurdles that regularly occur in organic synthesis are atom economy and novel and efficient reactions, which can answer both the ecological aspect and target-oriented synthesis (de Graaff et al, 2012;Lledó et al, 2019). Often traditional synthesis routes include multiple steps and long, tedious purification processes like column chromatography; these stages often add a significant amount of side products and also generate a huge amount of waste.…”

“…Major hurdles that regularly occur in organic synthesis are atom economy and novel and efficient reactions, which can answer both the ecological aspect and target-oriented synthesis ( de Graaff et al, 2012 ; Lledó et al, 2019 ). Often traditional synthesis routes include multiple steps and long, tedious purification processes like column chromatography; these stages often add a significant amount of side products and also generate a huge amount of waste.…”

Stereoselective synthesis of dispiroindano pyrrolidines by the [3 + 2] cycloaddition of thiazolo[3,2‐a]indole tethered dipolarophile with azomethine ylides

“…Of late there have been several attempts to employ green chemistry principles to azomethine ylide‐based [3 + 2] cycloadditions; already possessing the inherent advantage of a high degree of atom economy. Among these attempts, the use of ionic liquids [10], task‐specific ionic liquids (TSIL) [11] and deep eutectic solvents (DES) [12] as the reaction media are particularly noteworthy. Very recently, we had reported the stereoselective synthesis of dispiro heterocycles in DES by the [3 + 2] cycloaddition of isatin‐derived azomethine ylides with a thiazolo[3,2‐ a ]indole derivative 3 (Scheme 1) [13].…”