Aminopotassiation by Mixed Potassium/Lithium Amides: A Synthetic Path to Difficult to Access Phenethylamine Derivates
Insights gained from a comparison of aminometalation reactions with lithium amides, potassium amides and mixed lithium/potassium amides are presented. A combination of structural characterization, DFT calculations and electrophile reactions of aminometalated intermediates has shown the advantages of using a mixed metal strategy. While potassium amides fail to add, the lithium amides are uncontrollable and eliminated, yet the mixed K/Li amides deliver the best of both systems. Aminopotassiation proceeds to form the alkylpotassium species which has enhanced stability over its lithium counterpart allowing for its isolation and thereby its further characterization.
Brieger, Lukas,O'Shea, Donal F.,Opper, Ulrike,Otte, Felix,Seymen, Andreas,Strohmann, Carsten,Unkelbach, Christian,Vo?, Andreas
A potassium magnesiate complex: Synthesis, structure and catalytic intermolecular hydroamination of styrenes
A new heterobimetallic potassium magnesiate complex KMg[N(SiMe3)2]2Bn (Bn = PhCH2-) was synthesized by simply mixing magnesium amide and potassium benzyl in toluene. The TMEDA-ligated potassium magnesiate comple
Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali-Metal Amides under Air
A straightforward alkali-metal-mediated hydroamination of styrenes using biorenewable 2-methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method is also compatible with sodium amides, with the latter showing excellent promise as highly efficient catalysts under inert atmosphere conditions.
Bole, Leonie J.,Davin, Laia,García-álvarez, Joaquín,Hernán-Gómez, Alberto,Hevia, Eva,Kennedy, Alan,Mulks, Florian F.
p. 19021 - 19026
(2020/09/01)
ANTICANCER CALCIUM CHANNEL BLOCKERS
The present invention is directed to compounds useful as cancer cell inhibitors, compositions containing such compounds and methods for inhibiting proliferation of electrically non-excitable cells.
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Page 14
(2010/02/07)
Chemistry of dicationic electrophiles: superacid-catalyzed reactions of amino acetals.
Amino acetals are shown to form highly electrophilic systems in Bronsted superacids. It is proposed that amino acetals give dicationic electrophiles, and this proposal is supported by the direct observation of a dication by low-temperature (13)C NMR. When reacted with C(6)H(6) and superacidic CF(3)SO(3)H, amino acetals are shown to provide 1-(3,3-diphenylpropyl)amines and 1-(2,2-diphenylethyl)amines as condensation products in good yields (50-99%).
Klumpp, Douglas A,Sanchez Jr., Gregorio V,Aguirre, Sharon L,Zhang, Yun,de Leon, Sarah
p. 5028 - 5031
(2007/10/03)
Synthesis of aryl-substituted piperidines by superacid activation of piperidones
Diarylpiperidines (8-12) may be prepared in good to excellent yields (80-99%) by the reaction of piperidones (3d-h) with benzene and the Bronsted superacid, trifluoromethanesulfonic acid (CF3-SO3H, TfOH). Tropinone (6) and quinuclidone (7) also react in good yields with benzene in TfOH to give the condensation products (13 and 14). Ketal and acetal derivatives also give condensation products (8 and 24) upon reaction with C6H6 in TfOH. The conversion of 3g to 11 is sensitive to both acid quantity and acid strength; a mechanism is proposed for the conversion that invokes dicationic intermediates.
Klumpp, Douglas A.,Garza, Manuel,Jones, Andre,Mendoza, Saray
p. 6702 - 6705
(2007/10/03)
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