Selective formation of g-lactams via C–H amidation enabled by tailored iridium catalysts Highly Cited Paper Hot Paper

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Title
Selective formation of g-lactams via C–H amidation enabled by tailored iridium catalysts
Author(s)
Seung Youn Hong; Yoonsu Park; Yeongyu Hwang; Yeong Bum Kim; Mu-Hyun Baik; Sukbok Chang
Publication Date
2018-03
Journal
SCIENCE, v.359, no.6379, pp.1016 - 1021
Publisher
AMER ASSOC ADVANCEMENT SCIENCE
Abstract
Intramolecular insertion of metal nitrenes into carbon-hydrogen bonds to form g-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 g-lactams via sp3 and sp2 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.
URI
https://pr.ibs.re.kr/handle/8788114/4997
ISSN
0036-8075
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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