Electrosynthetic C− O bond activation in alcohols and alcohol derivatives

P Villo, A Shatskiy, MD Kärkäs… - Angewandte Chemie …, 2023 - Wiley Online Library
Alcohols and their derivatives are ubiquitous and versatile motifs in organic synthesis.
Deoxygenative transformations of these compounds are often challenging due to the …

New frontiers in organosodium chemistry as sustainable alternatives to organolithium reagents

DE Anderson, A Tortajada… - Angewandte Chemie …, 2024 - Wiley Online Library
With their highly reactive respective C− Na and N− Na bonds, organosodium and sodium
amide reagents could be viewed as obvious replacements or even superior reagents to the …

Highly reactive hydrocarbon soluble alkylsodium reagents for benzylic aroylation of toluenes using Weinreb amides

DE Anderson, A Tortajada… - Angewandte Chemie …, 2023 - Wiley Online Library
Deaggregating the alkyl sodium NaCH2SiMe3 with polydentate nitrogen ligands enables
the preparation and characterisation of new, hydrocarbon soluble chelated alkylsodium …

Synthesis of trans-1,2-dimetalloalkenes through reductive anti-dimagnesiation and dialumination of alkynes

F Takahashi, T Kurogi, H Yorimitsu - Nature Synthesis, 2023 - nature.com
Polar reactive organometallic species have been key reagents in synthesis for more than a
century. Stereodefined 1, 2-dimetallated alkenes offer promising synthetic utility; however …

Introducing water and deep eutectic solvents in organosodium chemistry: Chemoselective nucleophilic functionalizations in air

G Dilauro, C Luccarelli, AF Quivelli… - Angewandte Chemie …, 2023 - Wiley Online Library
Advancing the development of perfecting the use of polar organometallics in bio‐inspired
solvents, we report on the effective generation in batch of organosodium compounds, by the …

Carbon–Nitrogen Bond Formation Using Sodium Hexamethyldisilazide: Solvent-Dependent Reactivities and Mechanisms

Q You, DB Collum - Journal of the American Chemical Society, 2023 - ACS Publications
The solvent-dependent reactivity of sodium hexamethyldisilazide (NaHMDS) toward carbon-
centered electrophiles reveals reactions that are poorly represented or unrepresented in the …

Enhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications

LJ Bole, A Tortajada, E Hevia - Angewandte Chemie, 2022 - Wiley Online Library
Abstract Though LiTMP (TMP= 2, 2′, 6, 6′‐tetramethylpiperidide) is a commonly used
amide, surprisingly the heavier NaTMP has hardly been utilised. Here, by mixing NaTMP …

Dual Basicity and Nucleophilicity of Organosodium Reagents in Benzylic C− H Additions of Toluenes to Diarylethenes and Ketones

DE Anderson, AHN Truong… - Chemistry–A European …, 2024 - Wiley Online Library
Profiting from the dual high basicity and nucleophilicity of organosodium complexes, here
we report the stepwise lateral metalation of a wide range of alkyl arenes (MeAr), mediated …

Sodium Alkyl (trimethylsilyl) amides: Substituent-and Solvent-dependent Solution Structures and Reactivities

Q You, Y Ma, RA Woltornist, NM Lui… - Journal of the …, 2024 - ACS Publications
The preparation of sodium isopropyl (trimethylsilyl) amide (NaPTA), sodium (1-phenylethyl)(
trimethylsilyl) amide (NaPETA), sodium tert-butyl (trimethylsilyl) amide (NaBTA), and …

Gram‐Scale Synthesis, Isolation and Characterisation of Sodium Organometallics: nBuNa and NaTMP

A Tortajada, DE Anderson, E Hevia - Helvetica Chimica Acta, 2022 - Wiley Online Library
Organolithium compounds represent one of the most widely utilised commodity reagents in
synthetic chemistry. However, their analogues with the heavier alkali‐metal sodium are …