Ruthenium‐Alkylidene Complexes with Sterically Rigid Fluorinated NHC Ligands

Masoud, Salekh M.; Akmalov, Timur R.; Palagin, Konstantin A.; Dolgushin, Fedor M.; Нефедов, С. Е.; Osipov, Sergey N.

doi:10.1002/ejoc.201801116

Cited by 11 publications

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

et al. 2022

View full text Add to dashboard Cite

Imidazolium salts have ubiquitous applications in energy research, catalysis, materials and medicinal sciences. Here, we report a new strategy for the synthesis of diverse heteroatom‐functionalized imidazolium and imidazolinium salts from easily available 1,4‐diaza‐1,3‐butadienes in one step. The strategy relies on a discovered family of unprecedented nucleophilic addition/cyclization reactions with trialkyl orthoformates and heteroatomic nucleophiles. To probe general areas of application, synthesized N‐heterocyclic carbene (NHC) precursors were feasible for direct metallation to give functionalized M/carbene complexes (M=Pd, Ni, Cu, Ag, Au), which were isolated in individual form. The utility of the chloromethyl function for the postmodification of the synthesized salts and Pd/carbene complexes was demonstrated. The obtained complexes and imidazolium salts demonstrated good activities in Pd‐ or Ni‐catalyzed model cross‐coupling and C−H activation reactions.

show abstract

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

et al. 2022

View full text Add to dashboard Cite

show abstract

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

et al. 2022

View full text Add to dashboard Cite

Imidazolium salts have ubiquitous applications in energy research, catalysis, materials and medicinal sciences. Here, we report a new strategy for the synthesis of diverse heteroatom-functionalized imidazolium and imidazolinium salts from easily available 1,4-diaza-1,3-butadienes in one step. The strategy relies on a discovered family of unprecedented nucleophilic addition/cyclization reactions with trialkyl orthoformates and heteroatomic nucleophiles. To probe general areas of application, synthesized N-heterocyclic carbene (NHC) precursors were feasible for direct metallation to give functionalized M/carbene complexes (M = Pd, Ni, Cu, Ag, Au), which were isolated in individual form. The utility of the chloromethyl function for the postmodification of the synthesized salts and Pd/carbene complexes was demonstrated. The obtained complexes and imidazolium salts demonstrated good activities in Pd-or Ni-catalyzed model cross-coupling and CÀ H activation reactions.

show abstract

Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex

et al. 2018

Self Cite

View full text Add to dashboard Cite

A highly efficient and environmentally benign protocol for copper‐catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New copper(I) complexes bearing NHC ligands decorated with bulky hexafluoroisopropylalkoxy group [(CF3)2(OR)C‐] were first introduced for the process. The complex with isopentyl group [(CF3)2(OiAm)C‐] exhibited the best catalytic activity in the reactions of diversely substituted alkyne and azide substrates in alkane solvents, such as hexane, heptane and cyclohexane. The new CuAAC protocol is easily scalable, synthetically robust, and reproducible; it utilizes low catalyst loadings and enables simple isolation of pure products free from any contaminants including residue of the catalyst and starting materials.

show abstract

Ruthenium‐Alkylidene Complexes with Sterically Rigid Fluorinated NHC Ligands

Cited by 11 publications

References 64 publications

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex

Contact Info

Product

Resources

About