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• W3123454921 abstract "Abstract A series of pharmaceutically relevant small molecules 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 13 C‐labeled Ni II ‐acyl complexes, formed from a 13 CO insertion step with Ni II ‐alkyl intermediates, rapidly react in less than one minute with 2,2’‐dipyridyl disulfide to quantitatively form the corresponding 2‐pyridyl thioesters. Either the use of 13 C‐SilaCOgen or 13 C‐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 13 C‐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 chemistry for carbon‐11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of 13 C‐labeled liraglutide and insulin degludec, representing two antidiabetic drugs." @default.
• W3123454921 created "2021-02-01" @default.
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• W3123454921 date "2021-02-25" @default.
• W3123454921 modified "2023-10-11" @default.
• W3123454921 title "A Nickel(II)‐Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides" @default.
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• W3123454921 doi "https://doi.org/10.1002/chem.202005261" @default.
• W3123454921 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33452676" @default.
• W3123454921 hasPublicationYear "2021" @default.
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