In 2022,Kato, Daiki; Murase, Tomoya; Talode, Jalindar; Nagae, Haruki; Tsurugi, Hayato; Seki, Masahiko; Mashima, Kazushi published an article in Chemistry – A European Journal. The title of the article was 《Diarylcuprates for Selective Syntheses of Multifunctionalized Ketones from Thioesters under Mild Conditions》.Quality Control of 4-Iodobenzoic acid The author mentioned the following in the article:
Ketones were selectively synthesized from thioesters by using diarylcuprates(I) generated in situ from copper(I) salts and aryl Grignard reagents in a 1 : 1.3-1.5 ratio under ambient temperature During the ketone synthesis, various functional groups, such as carbonyl (ketones, esters, and amides), O-protecting groups, halogens, and heteroarenes, were tolerated to afford multifunctionalized ketones in excellent yields. This copper-mediated ketone synthesis could be applied to the synthesis of not only gluconolactone-derived ketone, a synthetic intermediate in the transformation to the SGLT2 inhibitor canagliflozin, but also thiolactol, a valuable synthetic intermediate for (+)-biotin. Control experiments on an isolated diphenylcuprate(I), [CuPh2]-, and DFT calculations revealed that this ketone synthesis proceeded by oxidative addition of the C-S bond of thioesters to [CuPh2]-, while reductive elimination from the CuIII intermediate produced the corresponding ketone and an inactive species [(RS)CuPh]-, the latter reacted with [CuPh]4 to regenerate the reactive diphenylcuprate(I). In addition to this study using 4-Iodobenzoic acid, there are many other studies that have used 4-Iodobenzoic acid(cas: 619-58-9Quality Control of 4-Iodobenzoic acid) was used in this study.
4-Iodobenzoic acid(cas: 619-58-9) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Quality Control of 4-Iodobenzoic acidIodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com