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Selective formation of γ-lactams via C–H amidation enabled by tailored iridium catalysts : Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts

Cited 251 time in Web of Science Cited 252 time in Scopus
Authors

Hong, Seung Youn; Park, Yoonsu; Hwang, Yeongyu; Kim, Yeong Bum; Baik, Mu-Hyun; Chang, Sukbok

Issue Date
2018-03
Publisher
American Association for the Advancement of Science
Citation
Science, Vol.359 No.6379, pp.1016-1021
Abstract
Intramolecular insertion of metal nitrenes into carbon-hydrogen bonds to form gamma-lactam rings has traditionally been hindered bycompeting isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding gamma-lactams via sp(3) and sp(2) C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.
ISSN
0036-8075
URI
https://hdl.handle.net/10371/191840
DOI
https://doi.org/10.1126/science.aap7503
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  • College of Natural Sciences
  • Department of Chemistry
Research Area Computational Modeling, Inorganic Chemistry, Molecular Catalysis, Organic Synthesis

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