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Prakash Sultane
다차원 탄소재료 연구단
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Cyclic (Aryl)(Amido)Carbenes: NHCs with Triplet-like Reactivity

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Title
Cyclic (Aryl)(Amido)Carbenes: NHCs with Triplet-like Reactivity
Author(s)
Prakash R. Sultane; Guillermo Ahumada; Janssen-Muller, D; Christopher W. Bielawski
Publication Date
2019-11
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.45, pp.16320 - 16325
Publisher
WILEY-V C H VERLAG GMBH
Abstract
The synthesis and study of a library of cyclic (aryl)(amido)carbenes (CArAmCs), which represent a class of electrophilic NHCs that feature low calculated singlet-triplet gaps (Delta E-ST=19.9 kcal mol(-1); B3LYP/def2-TZVP) and exhibit reactivity profiles expected from triplet carbenes, are described. The electrophilic properties of the CArAmCs were quantified by analyzing their respective selenium adducts, which exhibited the largest downfield Se-77 NMR chemical shifts (up to 1645 ppm) measured for any NHC derivative known to date, as well as their Ir carbonyl complexes, from which large Tolman electronic parameter (TEP) values (up to 2064 cm(-1)) were ascertained. The CArAmCs were found to engage in reactions that are typically observed with triplet carbenes, including C-H insertions, [2+1] cycloadditions with alkenes as well as alkynes, and spontaneous oxidation upon exposure to oxygen. C. 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/6406
ISSN
1433-7851
Appears in Collections:
Center for Multidimensional Carbon Materials(다차원 탄소재료 연구단) > Journal Papers (저널논문)
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