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Direct Access to Isotopically Labeled Aliphatic Ketones Mediated by Nickel(I) Activation
Author(s) -
Donslund Aske S.,
Pedersen Simon S.,
Gaardbo Cecilie,
Neumann Karoline T.,
Kingston Lee,
Elmore Charles S.,
Skrydstrup Troels
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201916391
Subject(s) - chemistry , alkyl , nickel , pincer movement , stoichiometry , radical , carbonylation , primary (astronomy) , carbon fibers , functional group , medicinal chemistry , organic chemistry , catalysis , carbon monoxide , materials science , physics , polymer , astronomy , composite number , composite material
An extensive range of functionalized aliphatic ketones with good functional‐group tolerance has been prepared by a Ni I ‐promoted coupling of either primary or secondary alkyl iodides with NN 2 pincer Ni II ‐acyl complexes. The latter were easily accessed from the corresponding Ni II ‐alkyl complexes with stoichiometric CO. This Ni‐mediated carbonylative coupling is adaptable to late‐stage carbon isotope labeling, as illustrated by the preparation of isotopically labelled pharmaceuticals. Preliminary investigations suggest the intermediacy of carbon‐centered radicals.