Iron-Catalyzed C(sp2)-H Alkylation of Indolines and Benzo[h]quinoline with Unactivated Alkyl Chlorides through Chelation Assistance was written by Jagtap, Rahul A.;Samal, Pragnya Paramita;Vinod, C. P.;Krishnamurty, Sailaja;Punji, Benudhar. And the article was included in ACS Catalysis in 2020.Application In Synthesis of 1-Bromo-6-chlorohexane The following contents are mentioned in the article:
Regioselective C-H bond alkylation of indolines and benzo[h]quinoline with a wide range of unactivated and highly demanded primary and secondary alkyl chlorides is accomplished using a low-cost iron catalyst. This reaction tolerates diverse functionalities, such as C(sp2)-Cl, fluoro, alkenyl, silyl, ether, thioether, pyrrolyl, and carbazolyl groups including cyclic and acyclic alkyls as well as alkyl-bearing fatty-alc. and polycyclic-steroid moieties. The demonstrated iron-catalyzed protocol proceeded via either a five-membered or a six-membered metallacycle. Intriguingly, the C-7-alkylated indolines can be readily functionalized into free-NH indolines/indoles and tryptamine derivatives A detailed mechanistic investigation highlights the participation of an active Fe(I) catalyst and the involvement of a halogen-atom transfer process via a single-electron-based mechanism. Deuterium labeling and kinetics anal. indicate that the C-H metalation of indoline is the probable turnover-limiting step. Overall, the exptl. and theor. studies supported an Fe(I)/Fe(III) pathway for the alkylation reaction comprising the two-step, one-electron oxidative addition of alkyl chloride. This study involved multiple reactions and reactants, such as 1-Bromo-6-chlorohexane (cas: 6294-17-3Application In Synthesis of 1-Bromo-6-chlorohexane).
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. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Application In Synthesis of 1-Bromo-6-chlorohexane
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics