Copper-catalyzed <i>O</i>-alkenylation of phosphonates

Vázquez‐Galiñanes, Nuria; Andón-Rodríguez, Mariña; Gómez-Roibás, Patricia; Fañanás‐Mastral, Martín

doi:10.3762/bjoc.16.56

Cited by 4 publications

(2 citation statements)

References 37 publications

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“…This strategy was then extended by Fananas-Mastral to the direct alkenylation of phosphonates by using unsymmetric styryl(aryl)iodonium reagents (Scheme 109) [150]. As usual, the presence of a non-transferable mesityl ligand on the asymmetric iodonium salt was crucial for the outcome of the reaction.…”

Section: Hypervalent Iodine As Reagent In C-o Bond Formationmentioning

confidence: 99%

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Papis,

Foschi,

Colombo

et al. 2023

Catalysts

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The functionalization of unactivated substrates through the combination of copper catalysts and hypervalent iodine reagents represents a versatile tool in organic synthesis to access various classes of compounds. The hypervalent iodine derivatives can be used simply as oxidizing agents to regenerate the catalytic species or they can associate the functionalization of the starting material. In this review, special attention will be paid to methodologies which provide the introduction of nucleophiles into the reagent by use of suitable benziodoxol(on)es or iodonium salts. Many reactions concern C- and N-arylations, but may also involve formation of different carbon–carbon and carbon–nitrogen bonds, carbon–oxygen as well as carbon–halogen and carbon–phosphorus bonds.

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Section: Hypervalent Iodine As Reagent In C-o Bond Formationmentioning

confidence: 99%

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Papis,

Foschi,

Colombo

et al. 2023

Catalysts

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“…Mechanistically, Cu(I) catalyst adds to mesitylvinyliodonium triflate to give vinylcopper(III) species. Then, alkenylcopper(III) species react with dialkyl phosphonate; resulting phosphonium intermediate which undergo Arbuzov‐type substitution of alkyl group and lastly, reductive elimination generates enol phosphate with regeneration of Cu(I) catalyst [27] …”

Section: Transformations Involving Hypervalent Iodine Reagents and 1s...mentioning

confidence: 99%

Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

et al. 2022

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This review outlines the progress over recent years in the reactions involving combined approach of hypervalent iodine reagents and transition metals such as palladium, nickel, iridium, gold, rhodium, copper, iron, ruthenium, platinum, silver, zinc, rhenium and cobalt. This approach enables organic transformations complimentary to traditional manifolds. Hypervalent iodine reagents play a preeminent role in organic chemistry due to their versatile reactivity, heteroatom ligands and mild reaction conditions. These reagents in combination of transition metal compounds are used in many synthetically useful organic reactions such as oxidation, rearrangement, amination, halogenation, amidation, ring-opening, cyclization and CÀ H and CÀ C functionalization reactions, etc. which are discussed here. Combination with Cobalt 2.3. Reactions of Hypervalent Iodine Reagents with Copper 2.4. Reactions of Hypervalent Iodine Reagents in Combination with Nickel 2.5. Reactions of Hypervalent Iodine Reagents in Combination with Zinc 3. Transformations Involving Hypervalent Iodine Reagents and 2 nd Transition Series Metals 3.1. Reactions of Hypervalent Iodine Reagents in Combination with Ruthenium 3.2. Reactions of Hypervalent Iodine Reagents in Combination With Rhodium 3.3. Reactions of Hypervalent Iodine Reagent in Combination With Palladium 3.4. Reactions of Hypervalent Iodine Reagents in Combination with Silver 4. Transformations Involving Hypervalent Iodine Reagents and 3rd Transition Series Metals 4.1. Reactions of Hypervalent Iodine Reagents in Combination with Rhenium 4.2. Reactions of Hypervalent Iodine Reagents in Combination with Iridium 4.3. Reactions of Hypervalent Iodine Reagents in Combination with Platinum 4.4. Reactions of Hypervalent Iodine Reagents in Combination with Gold 5. Conclusion

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Laser-induced twisting of phosphorus functionalized thiazolotriazole as a way of cholinesterase activity change

Pankin

Khokhlova

Kolesnikov

et al. 2021

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Copper-catalyzed O-alkenylation of phosphonates

Cited by 4 publications

References 37 publications

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

Laser-induced twisting of phosphorus functionalized thiazolotriazole as a way of cholinesterase activity change

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