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Jeonghyo, Lee
분자활성 촉매반응 연구단
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Alcohol-Incorporating Diels-Alder Dimerization of In Situ Formed ortho-Quinamine via Co-Nitrenoid Insertion

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Title
Alcohol-Incorporating Diels-Alder Dimerization of In Situ Formed ortho-Quinamine via Co-Nitrenoid Insertion
Author(s)
Jeonghyo Lee; Bora Kang; Dongwook Kim; Sukbok Chang
Publication Date
2022-08
Journal
ORGANIC LETTERS, v.24, no.31, pp.5845 - 5850
Publisher
AMER CHEMICAL SOC
Abstract
We disclose herein a Cp*Co(III)(LX)-catalyzed dearomative Diels-Alder dimerization of 2,6-disubstituted phenyl azidoformates. Upon the postulated cobalt-nitrenoid insertion into the neighboring ortho-carbon, the key intermediate of ortho-quinamine was generated for the subsequent dimeric cycloaddition process. A series of experimental and computational studies suggested that the quinolinol ligand of the cobalt catalyst plays a crucial role in the alcoholic solvent incorporation into the o-quinamine moiety, thereby enabling the Diels- Alder dimerization to furnish the bridged tricyclic bisamidation products.
URI
https://pr.ibs.re.kr/handle/8788114/12376
DOI
10.1021/acs.orglett.2c02392
ISSN
1523-7060
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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