Nickel-catalyzed C-H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(I)/Ni(III) pathway was written by Pandey, Dilip K.;Ankade, Shidheshwar B.;Ali, Abad;Vinod, C. P.;Punji, Benudhar. And the article was included in Chemical Science in 2019.HPLC of Formula: 10297-05-9 This article mentions the following:
A mild and efficient nickel-catalyzed method for the coupling of inactivated primary ClCH2R (R = 1-naphthylmethyl, cyclopentyl, SiMe3, 2-furanylethyl, etc.) and secondary alkyl chlorides XCHR1R2 (X = Cl, Br; R1 = Me, Ph; R2 = Ph; R1R2 = cyclopropyl, cyclohexyl, cycloheptyl, bicyclo[2.2.1]heptan-2-yl) with the C-H bond of indoles I (R3 = H, Me, OMe, F; R4 = pyridin-2-yl, pyrazin-2-yl; R5 = H, Me) and N-pyridin-2-ylpyrrole is described to demonstrate a high level of chemo and regioselectivity. The reaction tolerates numerous functionalities, such as halide, alkenyl, alkynyl, ether, thioether, furanyl, pyrrolyl, indolyl and carbazolyl groups including acyclic and cyclic alkyls under the reaction conditions. Mechanistic investigation highlights that the alkylation proceeds through a single-electron transfer (SET) process with Ni(I)-species being the active catalyst. Overall, the alkylation follows a Ni(I)/Ni(III) pathway involving the rate-influencing two-step single-electron oxidative addition of alkyl chlorides. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9HPLC of Formula: 10297-05-9).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.HPLC of Formula: 10297-05-9
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com