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Upstream product

• 101741-01-9 1-(4-methoxyphenyl)decan-1-one 
• 112-29-8 1-bromo dodecane 
• 112-13-0 n-decanoyl chloride 
• 111-83-1 1-bromo-octane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1002-69-3 decyl chloride 
• 623-12-1 4-chloromethoxybenzene 
• 100-66-3 methoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 2050-77-3 Iododecane 
• 344453-19-6 n-decylzinc iodide 

Downstream Products

• 2985-57-1 4-decylphenol 

Relevant academic research and scientific papers

Cross-coupling of alkyl halides with aryl or alkyl Grignards catalyzed by dinuclear Ni(ii) complexes containing functionalized tripodal amine-pyrazolyl ligands

Structurally distinctive dinuclear Ni(ii) complexes with furan or thiophene tethered amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. All complexes are catalytically active towards cross-coupling of aryl/alkyl Grignard reagents with β-H containing alkyl halides at room temperature in the presence of N,N,N',N'- tetramethylethylenediamine (TMEDA). The catalytic efficacy of the complexes is dependent on the tether substituent at the central amine. Two species, Ni(ii) TMEDA and Mg(ii) TMEDA complexes, have been isolated from the catalytic reaction mixtures under different conditions. Some ligand-stabilized Ni(ii) and Mg(ii) bimetallic species have also been identified in the ESI-MS spectra.

Cross-coupling of non-activated chloroalkanes with aryl grignard reagents in the presence of iron/N-heterocyclic carbene catalysts

An efficient and high-yielding cross-coupling reaction of various primary, secondary, and tertiary alkyl chlorides with aryl Grignard reagents was achieved by using catalytic amounts of N-heterocyclic carbene ligands and iron salts. This reaction is a simple and efficient arylation method having applicability to a wide range of industrially abundant chloroalkanes, including polychloroalkanes, which are challenging substrates under conventional cross-coupling conditions.

Ligand effects on Negishi couplings of alkenyl halides

Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.

Suzuki-miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides

(Chemical Equation Presented) Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions wer

Iron-catalyzed alkylations of aromatic Grignard reagents

(Chemical Equation Presented) Any old iron: Two efficient iron-catalyzed cross-coupling reactions between aryl Grignard reagents and alkyl bromides were developed that are suitable for large-scale applications. The first procedure uses iron acetylacetonate and involves a cooperative effect between the two ligands N,N,N′,N′-tetramethylethylenediamine (TMEDA) and hexamethylenetetraamine (HMTA), while the second procedure uses [(FeCl 3)2(tmeda)3] as catalyst. 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

Amino alcohols as ligands for nickel-catalyzed Suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids

Suzuki cross-coupling reactions of an unprecedented array of unactivated primary and secondary alkyl halides (including challenging alkyl chlorides) can be accomplished through the use of nickel/amino alcohol-based catalysts. Both the nickel precatalyst and the amino alcohols (prolinol or trans-2-aminocyclohexanol) are commercially available and air-stable. In view of the remarkable diversity of amino alcohols that are readily accessible, this discovery may open the door to the rapid development of versatile catalysts for a wide range of cross-coupling processes. Copyright

Stille cross-coupling of activated alkyltin reagents under "ligandless" conditions

(Chemical Equation Presented) Monoalkyltins activated by a fluoride source are shown to be as reactive as their vinyl or aryl homologues in the Stille coupling reaction, thus providing an easy entry into the pallado-catalyzed formation of Csp3-Csp2 bonds. In addition to this uncommon reactivity, this methodology holds several advantages such as (i) a quantitative preparation of stable and easy to handle alkyltin reagents 2, (ii) a simplified coupling procedure without any phosphine added ligand under neutral conditions, and (iii) a facile purification step of the organic products from the inorganic nontoxic tin byproducts.