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Relevant academic research and scientific papers

Iron-Catalyzed Cross-Coupling of Functionalized Benzylmanganese Halides with Alkenyl Iodides, Bromides, and Triflates

Various substituted benzylic manganese chlorides were prepared by insertion of magnesium turnings in the presence of MnCl2·2LiCl in THF at -5 °C within 2 h. These benzylic manganese reagents underwent smooth cross-couplings with various functionalized alkenyl iodides, bromides, and triflates or iodoacrylates in the presence of 10 mol % FeCl2 at 25 °C for 1-12 h. Mechanistic studies showed that benzylic manganese halides produced, in the presence of FeCl2, a very reactive iron ate complex.

Cross-Coupling Reactions of Alkenyl Halides with 4-Benzyl-1,4- Dihydropyridines Associated with E to Z Isomerization under Nickel and Photoredox Catalysis

Cross-coupling reactions of alkenyl halides with 4-alkyl-1,4-dihydropyridines as alkylation reagents have been achieved by combination of nickel and photoredox catalysts. Alkenyl halides bearing alkyl and aryl substituents are available. Particularly, in

Iron-Catalyzed Grignard Cross-Couplings with Allylic Methyl Ethers or Allylic Trimethylsilyl Ethers

We have found that cross-coupling between aryl Grignard reagents and allylic methyl ethers proceeded well in the presence of a catalytic amounts of Fe(acac) 3 to afford the corresponding allylic substitution products in good yields. Under the same conditions, allylic trimethylsilyl ethers also reacted with Grignard reagents to give the corresponding cross-coupling products.

Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3-Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed. (Chemical Equation Presented).

Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.

Grignard allylic substitution reaction catalyzed by 1,2,3-triazol-5-ylidene magnesium complexes

Allylic chlorides and phosphates reacted with alkyl-Grignard reagent in an SN2′-selective manner in the presence of a catalytic amount of 1,2,3-triazol-5-ylidenes to provide α-branched alkenes. Copyright

Grignard allylic substitution catalyzed by imidazol-2-ylidene- and imidazol-4-ylidene-magnesium complexes

In the presence of a catalytic amount of 1,2-disubstituted or 1,2,3-trisubstituted imidazolium salts, γ-substituted allyl chlorides reacted with alkyl Grignard reagents to undergo substitution reactions in an SN2′-selective fashion, where the magnesium ate complexes [(N-heterocyclic carbene-MgR3)-(MgX)+] of imidazol-2-ylidenes or imidazol-4-ylidenes, generated in situ, were postulated as the active species. It was observed that the reactions with imidazol-4-ylidene catalysts were faster than those with imidazol-2-ylidenes. Enantioselective catalysis using a chiral imidazolium salt was preliminarily investigated.

Cross-coupling reaction of allylic and benzylic carbonates with organo[2-(hydroxymethyl)phenyl]dimethylsilanes

The title reaction is found to proceed in the presence of a palladium catalyst and in the absence of any activator. Various functional groups are tolerated to give a diverse range of 1,4-diene and diarylmethane products, which are ubiquitous units of natural products and pharmaceuticals. Copyright

γ-Selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis

The reaction of allylic compounds with alkyl Grignard reagents in the presence of a catalytic amount of copper N-heterocyclic carbene (NHC) complexes proceeded predominantly in an SN2′ reaction pathway to give γ-substituted product in excellent

Allylated aromatics via Ni-catalyzed couplings of benzylic chlorides and vinylic organometallics

Hydroalumination and hydrozirconation of alkynes lead to vinylic organometallics which react with benzylic chlorides at room temperature under the influence of in situ-generated, catalytic quantities of (presumably) Ni(O), to afford allylated aromatics in good yields.