177969-49-2

Upstream product

• 111-83-1 1-bromo-octane 
• 28741-08-4 n-octylboronic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 2633-66-1 2-mesitylmagnesium bromide 
• 852142-68-8 (η¹-mesityl)₂Fe(κ²-TMEDA) 

Downstream Products

• 177969-52-7 2,4,6-trimethyl-3-n-octylbenzoic acid 

Relevant academic research and scientific papers

TMEDA in iron-catalyzed Kumada coupling: Amine adduct versus homoleptic "ate" complex formation

The reactions of iron chlorides with mesityl Grignard reagents and tetramethylethylenediamine (TMEDA) under catalytically relevant conditions tend to yield the homoleptic "ate" complex [Fe(mes)3] - (mes=mesityl) rather than adducts of the diamine, and it is this ate complex that accounts for the catalytic activity. Both [Fe(mes) 3]- and the related complex [Fe(Bn)3] - (Bn=benzyl) react faster with representative electrophiles than the equivalent neutral [FeR2(TMEDA)] complexes. FeI species are observed under catalytically relevant conditions with both benzyl and smaller aryl Grignard reagents. The X-ray structures of [Fe(Bn) 3]- and [Fe(Bn)4]- were determined; [Fe(Bn)4]- is the first homoleptic σ-hydrocarbyl FeIII complex that has been structurally characterized. Casting iron in catalytic roles: Chelating diamine ligands such as TMEDA are routinely used in iron-catalyzed cross-coupling reactions of aryl Grignard reagents. However, it was found that under catalytically relevant conditions, there is little evidence for their coordination to iron centers; homoleptic anionic organoiron species are produced instead. Copyright

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.

Iron-catalyzed grignard cross-coupling with alkyl halides possessing β-hydrogens

Tris(acetylacetonato)iron(III) (Fe(acac)3) was found to be an efficient catalyst for the cross-coupling reaction between aryl Grignard reagents and alkyl halides possessing β-hydrogens. The reaction is applicable to secondary alkyl halides as well as primary ones.

Process for the preparation of alkylated aromatic carboxylic acids and acyl halides

The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I STR1 wherein R1, R2, R3, R4 and R5 are each independently of one another hydrogen, C1 -C20 alkyl, halogen or C5 -C8 cycloalkyl, with the proviso that at least two of the substituents R1, R2, R3, R4 or R5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.