34577-40-7

Usage

Classification

Psychoactive stimulant drug

Effects

Increases mental alertness and physical energy

Uses

Treatment for ADHD and narcolepsy

Abuse

Commonly abused as a recreational drug for mood and concentration effects

Mechanism of action

Increases dopamine and norepinephrine levels in the brain

Side effects

Addiction, cardiovascular problems, psychological dependence

Risk

Long-term use can lead to serious health issues

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 96-22-0 pentan-3-one 
• 6921-34-2 benzylmagnesium chloride 
• 1192-17-2 2,2-diethyloxirane 
• 140-29-4 phenylacetonitrile 
• 3112-88-7 Benzyl phenyl sulfone 
• 55791-06-5 benzyl mesylate 
• 7417-81-4 benzyl phenyl sulfoxide 
• 14642-79-6 benzyloxy-trimethylsilane 
• 51029-13-1 N-benzyl-N-methyl triflamide 
• 95-14-7 1,2,3-Benzotriazole 
• 100-52-7 benzaldehyde 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 33143-15-6 (2-ethylbut-1-en-1-yl)benzene 
• 736145-01-0 (S)-2-(1-Benzyl-1-ethyl-propoxycarbonylamino)-hexanoic acid methyl ester 
• 106591-63-3 (+/-)-2,2-diethyl-3t-phenyl-cyclopropane-r-carboxylic acid 
• 784182-09-8 {(S)-1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pentyl}-carbamic acid 1-benzyl-1-ethyl-propyl ester 
• 784182-06-5 (S)-2-(1-Benzyl-1-ethyl-propoxycarbonylamino)-hexanoic acid 
• 736143-95-6 ((S)-1-Hydroxymethyl-pentyl)-carbamic acid 1-benzyl-1-ethyl-propyl ester 
• 19031-65-3 3-Fluor-3-ethyl-4-phenyl-butan 
• 34586-12-4 3-Benzyl-pent-3-yl-hydroperoxide 

Relevant academic research and scientific papers

Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI

Grignard-type additions were readily achieved under the mediation of CuI (10 mol%) and samarium (2 equiv.) by employing various organohalides,e.g.benzyl, aryl, heterocyclic and aliphatic halides (Cl, Br or I), and diverse carbonyl compounds (e.g.carbonic esters, carboxylic esters, acid anhydrides, acyl chlorides, ketones, aldehydes, propylene epoxides and formamides) to afford alcohols, ketones and aldehydes, respectively, with high efficiency and chemoselectivity, in which the organosamarium intermediate might be involved.

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.

Lithiation reactions catalyzed by linear and cross-linked arene-based polymers. Generation of functionalized organolithium compounds

Lithiation of various substrates, such as chlorinated acetals, α-chloro ether, dichloro derivatives benzo-fused heterocycles, and allyl and benzyl derivatives, with excess lithium powder in the presence of a catalytic amount of soluble linear or insoluble cross-linked arene (naphthalene or biphenyl)-based polymers yields the expected organolithium intermediates. The latter react with electrophiles either in two steps or under Barbier-type reaction conditions to afford the corresponding adducts. The catalyst is easily recuperated by filtration at the end of the process, and the procedure can be regarded as a reasonable alternative to the use of free arenes as electron carrier in lithiation reactions.

Direct transformation of allylic and benzylic thiols, thioethers, and disulfides into organolithium compounds

The reaction of allylic and benzylic thiols 1, disulfides 3, and thioethers 4 and 5 with an excess of lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5mol%) afforded the corresponding allylic and benzylic organolithium reagents via reductive cleavage of the carbon-sulfur bond. The generated organolithium compounds gave the expected products 2 by reaction with several electrophiles followed by hydrolysis with water. The reaction conditions and the lithiation procedure (stepwise of Barbier-type process) depended on the starting sulfur containing compound.

Preparation of alcohols from sulfones and trialkylboranes

The reaction of sulfone anions with trialkylboranes followed by thermal isomerization of the obtained boron compounds in the presence of excess borane-methyl sulfide complex and by alkaline hydroperoxide oxidation yields primary alcohols.

A facile and highly efficient route to a traceless pi-arene chromium linker. Applications to synthetic and combinatorial chemistry.

[reaction--see text] A simple and efficient method for the attachment of functionalized arene chromium carbonyls to a polymeric support has been developed. A highly efficient solid-phase synthesis of tertiary alcohols and esters was performed in a traceless manner using this strategy. The linker-fabrication protocol permits simultaneous immobilization of various substrates on the solid support.

Generation of allylic and benzylic organolithium compounds by fluorine-lithium exchange: Reaction with electrophiles

The application of the naphthalene-catalysed lithiation methodology to allylic and benzylic fluorides 1 led to the corresponding allylic and benzylic organolithium reagents, which, in the presence of different electrophiles (Barbier-type reaction conditions), afforded the expected products 2 in moderate yields. The procedure was useful for the transformation of primary, secondary and tertiary benzylic fluorides into the corresponding lithium derivatives. When a two-step lithiation process was used (treatment of fluoride 1 with lithium and a catalytic amount of naphthalene, followed by addition of the electrophilic reagent), only Wurtz-type coupling products were formed.

Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives

The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [(i)PrCHO, (t)BuCHO, PhCHO, Me2CO, Et2CO, (CH2)5CO, Ph2CO, Me3SiCl] in THF at different temperatures (-78, -30 or 0°C) leads, after hydrolysis with water to the corresponding allylated or benzylated products (2).

Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C-Benzotriazole Bond Scission

Various TV-substituted benzotriazoles are transformed, by scission of the C-benzotriazole bond, into the corresponding carbanions by treatment with lithium. Thus, N-(diphenylmethyl)benzotriazole (1), N-benzylbenzotriazole (6), and N-allylbenzotriazole (10) all gave carbanions that reacted with diverse electrophiles to afford the corresponding products in good yields. This new methodology was successfully utilized to convert N-benzylbenzotriazole (6) and N-allylbenzotriazole (10) into dianion synthons by a sequential lithiation and reductive coupling and bis(benzotriazolyl)toluene (18) by double reductive couplings, demonstrating the synthetic potential of the present methodology.