147936-56-9Relevant articles and documents
Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non-Activated Aliphatic C?H Bonds via Metallocarbene Intermediates
Hernán-Gómez, Alberto,Rodríguez, Mònica,Parella, Teodor,Costas, Miquel
supporting information, p. 13904 - 13911 (2019/08/30)
Combining an electrophilic iron complex [Fe(Fpda)(THF)]2 (3) [Fpda=N,N′-bis(pentafluorophenyl)-o-phenylenediamide] with the pre-activation of α-alkyl-substituted α-diazoesters reagents by LiAl(ORF)4 [ORF=(OC(CF3)3] provides unprecedented access to selective iron-catalyzed intramolecular functionalization of strong alkyl C(sp3)?H bonds. Reactions occur at 25 °C via α-alkyl-metallocarbene intermediates, and with activity/selectivity levels similar to those of rhodium carboxylate catalysts. Mechanistic investigations reveal a crucial role of the lithium cation in the rate-determining formation of the electrophilic iron-carbene intermediate, which then proceeds by concerted insertion into the C?H bond.
Palladium-Catalyzed Asymmetric α-Arylation of Alkylnitriles
Jiao, Zhiwei,Chee, Kwok Wei,Zhou, Jianrong Steve
, p. 16240 - 16243 (2016/12/27)
Asymmetric arylation of alkylnitriles forms quaternary stereocenters in good enantiocontrol for the first time. A lithium heterodimer consisting of an alkylnitrile anion and a disilylamide ion is the actual species responsible for the stereodetermining transmetalation in the catalytic cycle.
Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction
Carroll, F. Ivy,Blough, Bruce E.,Abraham, Philip,Mills, Andrew C.,Holleman, J. Ashley,Wolckenhauer, Scott A.,Decker, Ann M.,Landavazo, Antonio,McElroy, K. Timothy,Navarro, Hernán A.,Gatch, Michael B.,Forster, Michael J.
supporting information; experimental part, p. 6768 - 6781 (2010/04/06)
A series of bupropion (1a) analogues (1b-1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H] dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DAuptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3- chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction. 2009 American Chemical Society.