1560-97-0

Usage

InChI:InChI=1/C13H28/c1-4-5-6-7-8-9-10-11-12-13(2)3/h13H,4-12H2,1-3H3

Upstream product

• 2050-77-3 Iododecane 
• 90334-42-2 acetone tritylhydrazone 
• 17049-50-2 n-decyl magnesium bromide 
• 75-26-3 isopropyl bromide 
• 693-58-3 1-Bromononane 
• 112-41-4 1-dodecene 
• 74087-34-6 nonyl methanesulfonate 
• 5674-02-2 2-methylpropylmagnesium chloride 
• 463-18-3 n-nonyl fluoride 
• 91-17-8 decalin 
• 112-29-8 1-bromo dodecane 
• 625-81-0 diisopropyl zinc 
• 100-52-7 benzaldehyde 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 

Relevant academic research and scientific papers

Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: Efficiency of catalyst and roles of additives

Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions.

Organochromium complexes as catalysts for the carboalumination of unactivated terminal olefins

The addition of aluminium alkyls to terminal olefins leads to branched organoaluminium compounds which can be converted into functionalised alkanes. This carboalumination reaction is efficiently catalysed by a donor functionalised Cp-chromium(III) complex

Cobalt-catalyzed cross-coupling reaction between functionalized primary and secondary alkyl halides and aliphatic Grignard reagents

The coupling of primary and secondary unactivated alkyl bromides with alkyl-Grignard reagents was performed in good yields under mild conditions by using a new catalytic system: consisting of cobalt chloride and tetramethylethylenediamine (CoCl2·2 LiI, 4TMEDA). The reaction is very chemoselective since ketone, ester and nitrile functions are tolerated.

Process for hydrogenation of carboxylic acids and derivatives to hydrocarbons

A process for hydrogenating a carboxylic acid and/or derivative thereof having a carboxylate group represented by the general formula R1COO-, which process comprises feeding hydrogen and the carboxylic acid and/or derivative thereof to a reactor and maintaining conditions within the reactor such that hydrogen reacts with the carboxylic acid and/or derivative thereof to produce a product stream comprising carbon dioxide, carbon monoxide, methane and hydrocarbons represented by general formulae R1H and R1CH3, characterised in that the molar ratio of R1H : R1CH3 is above a pre-determined value and/or the mole ratio of the sum of carbon dioxide, carbon monoxide and methane to carboxylate groups is above a pre-determined value.

Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne

(Chemical Equation Presented) A general get-together: The Cu-catalyzed cross-coupling reaction of primary-alkyl halides with primary-, secondary-, and tertiary-alkyl and phenyl Grignard reagents proceeds efficiently in THF under reflux in the presence of 1-phenylpropyne (see scheme). The reaction is also applicable to alkyl mesylates (OMs) and tosylates (OTs). The reactivities of alkyl-X with a Grignard reagent increase in the order X = Cl F OMs OTs Br.

Nickel-catalyzed cross-coupling reaction of alkyl halides with organozinc and grignard reagents with 1,3,8,10-tetraenes as additives

Essential additives: The addition of bis(1,3-butadienyl) compounds (tetraenes) was essential in the efficient Nicatalyzed cross-coupling of organozinc reagents with alkyl bromides and a tosylate (see scheme, X = C(CO2Me)2 or NCH2Ph). The efficiency of the Ni-catalyzed cross-coupling of an alkyl fluoride with a Grignard reagent was also improved by using these tetraenes.

Radical deoxygenation of tertiary alcohols via trifluoroacetates

Trifluoroacetates of tertiary alcohols undergo deoxygenation by Ph 2SiH2 in the presence of (tBuO)2 in excellent yields of the deoxy products without affecting the stereochemistry at β-carbon.

Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a Grignard reagent with an alkyl sulfonate

A mixture of equal amounts of CuBr-SMe2, LiBr, and LiSPh in THF at 0°C furnished a new soluble copper catalyst that was highly efficient at coupling primary, secondary, tertiary, aryl, vinyl, and allylic Grignard reagents to primary tosylates and primary Grignard reagents to secondary tosylates and mesylates, all with the use of only 1 equiv of Grignard reagent. The new catalyst was shown to be much more reactive than copper catalysts CuBr and Li2CuCl4 and more efficient in the transference of secondary and tertiary alkyl groups than lower order cuprates (Gilman reagents) and demonstrated more reactivity than the lower order cuprates with its ability to couple primary Grignard reagents to secondary sulfonates. The Grignard reagent/catalyst system was compatible with an ester functionalized tosylate, thus proving to be more chemoselective than a Grignard reagent without the catalyst. The catalyst exhibited good reactivity below room temperature, and with the addition of 6% v/v of HMPA to the catalyst solution, excellent yields of coupled product were obtained within a 25-67°C temperature range. 1H NMR demonstrated that the catalyst solution consisted of several species that most likely were composed of copper ligated with thiophenol, THF, and LiBr in aggregated forms.

Copper-catalyzed cross-coupling of alkylsamarium reagents with alkyl halides

SmI2/HMPA converts alkyl iodides and bromides to alkyl samarium reagents which can be cross-coupled with primary alkyl iodides and bromides and secondary iodides in the presence of Cu(I) halides or Li2CuCl4 at room temperature. The alkylation of primary iodides gives good yields of cross-coupling products with negligible home-coupling produces. The method is especially useful for the small scale cross-coupling reactions.