57775-05-0

Upstream product

• 994-79-6 tetrabutylsilane 
• 91-15-6 phthalonitrile 
• 1461-25-2 tetra-n-butyltin(IV) 
• 1067-42-1 tetrabutylgermanium 
• 542-69-8 1-iodo-butane 
• 873-32-5 2-Chlorobenzonitrile 
• 109-65-9 1-bromo-butane 
• 507-19-7 t-butyl bromide 
• 558-17-8 tert-Butyl iodide 
• 4426-47-5 butylboronic acid 
• 2042-37-7 o-cyanobromobenzene 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 1276042-22-8 1-propyl-4-p-tolylphthalazine 
• 1276042-18-2 1-propyl-3-p-tolyl-1H-isoindol-1-ol 

Relevant academic research and scientific papers

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere via N-H imines as an intramolecular directing group

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.

Reductive activation of arenes: XIX. Mechanism and some synthetic applications of the alkylation of phthalodinitrile radical anion

Using cyclopropylmethyl bromide as mechanism-sensitive reagent, it was shown that the reaction of phthalonitrile radical anion with alkyl halides in liquid ammonia involves electron transfer. The effects of the nature of alkyl bromide and counterion in th

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.

Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents

In the presence of manganese chloride (10%), Grignard reagents readily react in THF with aryl bromides, chlorides and even fluorides, as well as aryl methyl ethers bearing in the ortho- or para-position an electron withdrawing activating group (CN, CH=NR, oxazoline). Aryl and N- or S- alkylmagnesium halides have been used successfully. The reaction is performed under mild conditions (0 °C to room temperature, 30 minutes to 24 hours) and leads to cross-coupling products in good yields.

Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia

The product of one-electron reduction of the phthalonitrile with metallic potassium in liquid ammonia reacts with butyl halides (BuCl, BuBr, BuI, s-BuBr, t-BuBr, t-BuI) to yield compounds of alkyl bonding in ipso(2-butylbenzonitriles) and unsubstituted (4-butyl-1,2-dicyanobenzenes and 2,5-dibutylbenzonitriles) positions of the aromatic ring of the original dinitrile. The dependence of the product composition on the character of alkyl moiety and halogen atom in the butyl halide is rationalized by reaction mechanism including at the first stage electron transfer from the anion-radical of the phthalonitrile to the alkyl halide and followed by recombination of the alkyl radical produced with another molecule of anionradical.

NOVEL ALKYLATION OF AROMATIC NITRILES VIA PHOTO-INDUCED ELECTRON TRANSFER OF GROUP 14 METAL-CARBON ? DONORS

Photo-induced electron transfer reactions of tetraalkylsilanes, -germanes, and -stannanes with aromatic nitriles afforded alkylated products.The mechanism was investigated by use of a radical clock.