7206-28-2

Usage

InChI:InChI=1/C12H24/c1-3-5-7-9-11-12-10-8-6-4-2/h9,11H,3-8,10,12H2,1-2H3/b11-9+

Upstream product

• 19780-12-2 5-dodecyne 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 66-25-1 hexanal 
• 64531-23-3 1c-chloro-oct-1-ene 
• 693-04-9 butyl magnesium bromide 
• 52356-93-1 (Z)-1-octenyl iodide 
• 109-72-8 n-butyllithium 
• 407617-06-5 1,1-dibromo-2-(trimethylsiloxy)octane 
• 693-03-8 n-butyl magnesium bromide 
• 88708-53-6 1-(dodec-1-ylsulfanyl)-2-phenylethene 
• 42843-49-2 (Z)-1-bromo-1-octene 
• 125378-24-7 1-octenyl iodide 
• 1120-29-2 5,7-dodecadiyne 
• 592-41-6 1-hexene 

Relevant academic research and scientific papers

Single-Electron-Transfer-Induced Coupling of Alkylzinc Reagents with Aryl Iodides

Alkylzinc reagents prepared from an alkyllithium and zinc iodide were found to undergo coupling with aryl and alkenyl iodides in the presence of LiI in a mixed solvent consisting of THF and diglyme (1:1). Alkyllithiums, prepared by halogen–lithium exchange between an alkyl iodide and tert-butyllithium, are also converted to alkylarenes through alkylzinc reagents.

Copper-catalyzed semihydrogenation of alkynes to Z -alkenes

Copper-catalyzed semihydrogenation of internal alkynes has been developed. The reaction proceeds under an atmosphere of hydrogen (5 atm) at 100 °C in the presence of a readily available [(PPh3)CuCl]4 catalyst to give various Z-alkenes stereoselectively.

Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature

Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.

Iron thiolate complexes: Efficient catalysts for coupling alkenyl halides with alkyl grignard reagents

Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required. Copyright

Nickel-catalyzed cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl grignard reagents using (Z)-3,3-dimethyl-1,2- bis(diphenylphosphino)but-1-ene as ligand

A combination of nickel(II) acetylacetonate and (Z)-3,3-dimethyl-1,2- bis(diphenylphosphino)but-1-ene catalyzes cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl Grignard reagents. Not only primary but also secondary alkyl Grignard reagents can be employed. Georg Thieme Verlag Stuttgart.

Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: Synthesis of alkenes with high (Z)-selectivity through β-elimination reactions

(Chemical Equation Presented) The photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins is promoted by samarium diiodide. As a result of this, β-elimination of O-acetyl chlorohydrins is achieved, affording the corresponding (Z)-alkenes with total or high stereoselectivity.

Synthesis of trisubstituted and tetrasubstituted alkenes via a manganate-induced migration-elimination process

Preparation of alkenes via a manganate-induced alkylation-elimination sequence was investigated. The reaction of 2-alkoxy-1,1-dibromoalkanes with trialkylmanganates afforded disubstituted or trisubstituted alkenes. Treatment of 2-alkoxy-1,1,1-tribromoalkanes with trialkylmanganates provided trisubstituted or tetrasubstituted alkenes through bromine-metal exchange, transfer of two alkyl groups from manganese to carbon, and successive elimination of metal and the β-alkoxy moieties.

Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds

In the presence of Fe(acac)3, Grignard reagents react readily with alkenyl halides (X = I, Br or Cl) in a THF/NMP mixture to give the cross-coupling products in high yields with an excellent stereoselectivity (≤99.5%). The scope of the reaction is very broad since a vast array of functional groups are tolerated (esters, nitriles, aromatic or aliphatic halides and even ketones). The procedure reported herein is an interesting alternative to the classical Pd- or Ni-catalyzed reactions, especially for preparative organic chemistry.

Cobalt-catalyzed alkenylation of organomagnesium reagents

Alkenyl iodides, bromides and chlorides react with organomagnesium reagents in THF, in the presence of Co(acac)2 and NMP (9 to 4 equiv.), to give the cross-coupling products in good yields. The reaction is chemoselective (aryl or alkyl bromides, esters and ketones) and stereoselective (≤ 99.5%).

CATALYTIC HYDROGENATION OF ALKYNES TO CIS-ALKENES ON A MODIFIED BORON-NICKEL CATALYST

Hydrogenation of alkynes from decyne and dodecyne (C10-C12) with the triple bond at C3, C4, C5, and C6 led to the corresponding alkenes on a boron-nickel catalyst modified by a 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone (4-aminoantipyrene).The stereospecificity for formation of the cis-alkenes was 95-98percent.