A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides was written by Pedersen, Simon S.;Donslund, Aske S.;Mikkelsen, Jesper H.;Bakholm, Oskar S.;Papp, Florian;Jensen, Kim B.;Gustafsson, Magnus B. F.;Skrydstrup, Troels. And the article was included in Chemistry – A European Journal in 2021.Application In Synthesis of 15-Bromopentadecanoic acid This article mentions the following:
A series of pharmaceutically relevant small mols. and biopharmaceuticals bearing aliphatic carboxamides have been successfully labeled with carbon-13. Key to the success of this novel carbon isotope labeling technique is the observation that 13C-labeled Ni(II)-acyl complexes, formed from a 13CO insertion step with Ni(II)-alkyl intermediates, rapidly react in less than one minute with 2,2′-dipyridyl disulfide to quant. form the corresponding 2-pyridyl thioesters. Either the use of 13C-SilaCOgen or 13C-COgen allows for the stoichiometric addition of isotopically labeled carbon monoxide. Subsequent one-pot acylation of a series of structurally diverse amines provides the desired 13C-labeled carboxamides in good yields. A single electron transfer pathway is proposed between the Ni(II)-acyl complexes and the disulfide providing a reactive Ni(III)-acyl sulfide intermediate, which rapidly undergoes reductive elimination to the desired thioester. By further optimization of the reaction parameters, reaction times down to only 11 min were identified, opening up the possibility of exploring this chem. for carbon-11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of 13C-labeled liraglutide and insulin degludec, representing two antidiabetic drugs. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Application In Synthesis of 15-Bromopentadecanoic acid).
15-Bromopentadecanoic acid (cas: 56523-59-2) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Application In Synthesis of 15-Bromopentadecanoic acid
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary