Reductive Ring Opening of Arylcyclopropanecarboxamides Accompanied by Borylation and Enolate Formation

Article Chemistry, Multidisciplinary

Birch Reduction of Arenes Using Sodium Dispersion and DMI under Mild Conditions

Sobi Asako et al.

Summary: The combination of a sodium dispersion in paraffin oil and 1,3-dimethyl-2-imidazolidinone enables the Birch-type reduction of a variety of arenes with high yields, selectivity, and tolerance of functionality.

CHEMISTRY LETTERS (2022)

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Review Chemistry, Multidisciplinary

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Vincent Pirenne et al.

Summary: This review discusses the development of enantioselective methods for the ring opening of cyclopropanes, including reactions based on nonchiral cyclopropanes and asymmetric transformations of chiral substrates. It is organized according to substrate classes, focusing on both established and emerging methods for enantioselective ring opening reactions of different cyclopropanes.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Halogen-sodium exchange enables efficient access to organosodium compounds

Sobi Asako et al.

Summary: The halogen-sodium exchange method allows for the preparation of a variety of aryl and alkenylsodium compounds, including previously inaccessible products. The use of a unique alkylsodium compound with no beta-hydrogens has been shown to efficiently suppress undesired reactions and make the method convenient and widely applicable.

COMMUNICATIONS CHEMISTRY (2021)

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Article Chemistry, Organic

Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal

Shuo Wang et al.

Summary: Sodium dispersion promotes the reductive ring opening of arylcyclopropanes, leading to the formation of 1,3-difunctionalized 1-arylalkanes with the immediate trapping of reactive carbanions. The ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

SYNLETT (2021)

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Article Chemistry, Organic

Recent Advances in the Use of Sodium Dispersion for Organic Synthesis

Pinaki Bhusan De et al.

Summary: This short review discusses the recent emergence of organosodium chemistry driven by the need for sustainability in modern synthetic chemistry. Methods for preparing organosodium compounds using sodium dispersion and their applications in synthesis are presented, along with a brief discussion of sodium amides and phosphides.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Organic

Defluorinative Diborasodiation of Benzotrifluorides with Bis(pinacolato)Diboron and Sodium

Shiori Ito et al.

Summary: Treatment of benzotrifluorides with sodium dispersion in the presence of bis(pinacolato)diboron leads to diborative reduction to obtain diborylbenzylsodium species. These anionic species not only react with reactive organic halides, but also with aromatic carbonyl compounds to produce alkenylboron compounds via Peterson-type olefination. The key to the success of generating diborylbenzylsodium species lies in the immediate capture of unstable difluorobenzylsodium with co-existing reduction-resistant bis(pinacolato)diboron.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

Mizuki Fukazawa et al.

Summary: Sodium dispersion promotes the reductive borylation of polycyclic aromatic hydrocarbons, leading to the formation of diverse boron-containing products with unique properties. This method offers a new route to synthesizing borylated PAHs with novel characteristics, posing a potential rival to traditional C-X borylation and catalytic C-H borylation techniques.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

ON THE ORDER OF ADDITION OF SODIUM DISPERSION IN REDUCTIVE DIBORATIONS OF STILBENE AND 1,2-DIPHENYLCYCLOPROPANE

Shuo Wang et al.

Summary: Two extreme methods of adding sodium dispersion were investigated in the reactions, and while no significant differences were observed in four cases, this information would be helpful for larger-scale transformations.

HETEROCYCLES (2021)

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Review Chemistry, Organic