- Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
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Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)?N and C(sp2)?O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe and mild catalytic conditions. Finally, we employ electrochemical current measurements to perform a reaction progress kinetic analysis. This technique reveals that the improved activity of this new system is a consequence of an enhanced catalyst stability profile.
- Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.
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p. 21418 - 21425
(2021/08/25)
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- Direct benzylic metalation of a phenethylamine derivative: Potassium as the key to both generation and stabilization of a labile anion
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t-BuLi-t-BuOK selectively metalates the benzylic position of 2-phenylethyldimethylamine under mild conditions without occurrence of β-elimination in the resulting metalated species. Theoretical and structural studies indicate that potassium is crucial for both the lowering of the barrier of the initial deprotonation step and the stabilization of the labile anion.
- Unkelbach, Christian,Rosenbaum, Hannah S.,Strohmann, Carsten
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supporting information
p. 10612 - 10614,3
(2020/09/02)
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- 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity
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A series of 2-phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives was examined for the ability to inhibit both rat brain imipramine receptor binding and the synaptosomal uptake of norepinephrine (NE) and serotonin (5-HT). Neurotransmitter uptake inhibition was highest for a subset of 2-phenyl-2-(1-hydroxycyclohexyl)dimethylethylamines in which the aryl ring has a halogen or methoxy substituent at the 3- and/or 4-positions. Potential antidepressant activity in this subset was assayed in three rodent models - the antagonism of reserpine-induced hypothermia, the antagonism of histamine-induced ACTH release, and the ability to reduce noradrenergic responsiveness in the rat pineal gland. An acute effect seen in the rat pineal gland with several analogues, including 1-[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol (23) and 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (4), was taken as a possible correlate of a rapid onset of antidepressant activity. Compound 4 (venlafaxine) is presently undergoing clinical evaluation.
- Yardley,Morris Husbands,Stack,Butch,Bicksler,Moyer,Muth,Andree,Fletcher III,James,Sielecki
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p. 2899 - 2905
(2007/10/02)
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- 2-PHENYL-2-(1-HYDROXYCYCLOALKYL OR 1-HYDROXYCYCLOALK-2-ENYL)ETHYLAMINE DERIVATIVES
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This invention provides a group of hydroxycycloalkanephenethyl amine antidepressant derivatives of the following structural formula: STR1 in which A is a moiety of the formula STR2 where the dotted line represents optional unsaturation;R 1 is hydrogen or alkyl;R 2 is alkyl;R. sub.4 is hydrogen, alkyl, formyl or alkanoyl;R 5 and R 6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl or, taken together, methylenedioxy;R. sub.7 is hydrogen or alkyl; andn is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof.
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