Copper-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions Using Hydrocarbon Additives: Efficiency of Catalyst and Roles of Additives was written by Iwasaki, Takanori;Imanishi, Reiko;Shimizu, Ryohei;Kuniyasu, Hitoshi;Terao, Jun;Kambe, Nobuaki. And the article was included in Journal of Organic Chemistry in 2014.SDS of cas: 6294-17-3 The following contents are mentioned in the article:
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. This study involved multiple reactions and reactants, such as 1-Bromo-6-chlorohexane (cas: 6294-17-3SDS of cas: 6294-17-3).
1-Bromo-6-chlorohexane (cas: 6294-17-3) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.SDS of cas: 6294-17-3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics