ChemInform Abstract: Rhodium(III)‐Catalyzed ortho‐Alkenylation Through C—H Bond Cleavage Directed by Sulfoxide Groups.

Nobushige, Kazunori; Hirano, Koji; Satoh, Toshifumi; Miura, Masahiro

doi:10.1002/chin.201431094

Cited by 2 publications

(2 citation statements)

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“…ortho-Alkenylated phenylphosphine sulfides 191 and picolinamides 193 were synthesized via the alkenylation with internal alkynes at the ortho-position of phenylphosphine sulfides 190 (Scheme 94) 95 and picolinamides 192 (Scheme 95), 96 respectively. An analogous ortho-directing effect is demonstrated by the SO 2 group in the alkenylation of alkyl aryl or diaryl sulfones 194 (Scheme 96) 97 and by the SO group in alkyl aryl or diaryl sulfoxides 196 (Scheme 97), 98 providing alkenyl derivatives 195 and 197, respectively. phenone derivatives 202 and their subsequent coupling with internal alkynes (Scheme 99).…”

Section: Rhodium-catalyzed Reactionsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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This review is focused on the analysis of current data on new methods of alkenylation of arenes and heteroarenes with alkynes by transition metal catalyzed reactions, Bronsted/Lewis acid promoted transformations, and others. The synthetic potential, scope, limitations, and mechanistic problems of the alkenylation reactions are discussed. The insertion of an alkenyl group into aromatic and heteroaromatic rings by inter- or intramolecular ways provides a synthetic route to derivatives of styrene, stilbene, chalcone, cinnamic acid, various fused carbo- and heterocycles, etc.

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Section: Rhodium-catalyzed Reactionsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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“…32−34 Following functionalization, sulfoxide groups can be removed through deoxygenation, followed by desulfurization. 35,36 Deoxygenation of sulfoxides also plays a crucial role in the pharmaceutical chemistry. 37 For example, some sulfide-containing bioactive molecules, such as sulindac sulfide (anti-inflammatory drug) and ufiprazole (antiulcer drug), are synthesized by the deoxygenation of sulfoxide analogues.…”

Section: ■ Introductionmentioning

confidence: 99%

Phosphorus-Alloying as a Powerful Method for Designing Highly Active and Durable Metal Nanoparticle Catalysts for the Deoxygenation of Sulfoxides: Ligand and Ensemble Effects of Phosphorus

Ishikawa

Yamaguchi

Nakata

et al. 2022

JACS Au

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The modification of metal nanoparticles (NPs) by incorporating additional metals is a key technique for developing novel catalysts. However, the effects of incorporating nonmetals into metal NPs have not been widely explored, particularly in the field of organic synthesis. In this study, we demonstrate that phosphorus (P)-alloying significantly increases the activity of precious metal NPs for the deoxygenation of sulfoxides into sulfides. In particular, ruthenium phosphide NPs exhibit an excellent catalytic activity and high durability against sulfur-poisoning, outperforming conventional catalysts. Various sulfoxides, including drug intermediates, were deoxygenated to sulfides with excellent yields. Detailed investigations into the structure–activity relationship revealed that P-alloying plays a dual role: it establishes a ligand effect on the electron transfer from Ru to P, facilitating the production of active hydrogen species, and has an ensemble effect on the formation of the Ru–P bond, preventing strong coordination with sulfide products. These effects combine to increase the catalytic performance of ruthenium phosphide NPs. These results demonstrate that P-alloying is an efficient method to improve the metal NP catalysis for diverse organic synthesis.

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ChemInform Abstract: Rhodium(III)‐Catalyzed ortho‐Alkenylation Through C—H Bond Cleavage Directed by Sulfoxide Groups.

Cited by 2 publications

References 1 publication

Alkenylation of Arenes and Heteroarenes with Alkynes

Alkenylation of Arenes and Heteroarenes with Alkynes

Phosphorus-Alloying as a Powerful Method for Designing Highly Active and Durable Metal Nanoparticle Catalysts for the Deoxygenation of Sulfoxides: Ligand and Ensemble Effects of Phosphorus

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