379-57-7Relevant articles and documents
Shuttle arylation by Rh(I) catalyzed reversible carbon–carbon bond activation of unstrained alcohols
Lutz, Marius D.R.,Gasser, Valentina C.M.,Morandi, Bill
supporting information, p. 1108 - 1119 (2021/04/19)
The advent of transfer hydrogenation and borrowing hydrogen reactions paved the way to manipulate simple alcohols in previously unthinkable manners and circumvented the need for hydrogen gas. Analogously, transfer hydrocarbylation could greatly increase the versatility of tertiary alcohols. However, this reaction remains unexplored because of the challenges associated with the catalytic cleavage of unactivated C–C bonds. Herein, we report a rhodium(I)-catalyzed shuttle arylation cleaving the C(sp2)–C(sp3) bond in unstrained triaryl alcohols via a redox-neutral β-carbon elimination mechanism. A selective transfer hydrocarbylation of substituted (hetero)aryl groups from tertiary alcohols to ketones was realized, employing benign alcohols as latent C-nucleophiles. All preliminary mechanistic experiments support a reversible β-carbon elimination/migratory insertion mechanism. In a broader context, this novel reactivity offers a new platform for the manipulation of tertiary alcohols in catalysis.
Synthesis of symmetrical ketones from Grignard reagents and 1,1′-carbonyldiimidazole
Bottalico, Daniela,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
experimental part, p. 2316 - 2318 (2010/02/28)
Coupling reactions of 1,1′-carbonyldiimidazole with Grignard reagents provide a rapid and straightforward method for the synthesis of symmetrical ketones. Georg Thieme Verlag Stuttgart.
Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA uptake inhibitors: Identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT- 3
Dhar,Borden,Tyagarajan,Smith,Branchek,Weinshank,Gluchowski
, p. 2334 - 2342 (2007/10/02)
γ-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian central nervous system. Molecular biology has revealed the presence of four high-affinity GABA transporters in the brain, GAT-1, GAT-2, GAT-3, and BGT-1, the latter transporting both GABA and the osmolyte Betaine. We have shown that known GABA uptake inhibitors such as SK and F 89976-A, CI- 966, and Tiagabine exhibit high affinity and selectivity for GAT-1. In the present paper we describe the design and synthesis of a novel series of triarylnipecotic acid derivatives for evaluation as GABA uptake inhibitors. The design lead for this series of compounds was the nonselective GABA uptake inhibitor EGYT-3886, [(-)-2-phenyl-2-[(dimethylamino)ethoxy]-(1R)-1,7,7- trimethylbicyclo[2.2.1]heptane]. From this series of compounds (S)-1-[2- [tris(4-methoxyphenyl)methoxy]ethyl]-3-piperidinecarboxylic acid, 4(S) was identified as a novel ligand with selectivity for GAT-3. 4(S) displayed an IC50 of 5 μM at GAT-3, 21 μM at GAT-2, >200 μM at GAT-1, and 140 μM at BGT-1. This compound will be an important tool for evaluating the role of GAT-3 in neural function.
