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Gangadhar Rao Mathi
분자활성 촉매반응 연구단
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Photochemical Carbopyridylation of Alkenes Using N-Alkenoxypyridinium Salts as Bifunctional Reagents

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Title
Photochemical Carbopyridylation of Alkenes Using N-Alkenoxypyridinium Salts as Bifunctional Reagents
Author(s)
Gangadhar Rao Mathi; Yujin Jeong; Yonghoon Moon; Sungwoo Hong
Publication Date
2020-01
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.5, pp.2049 - 2054
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimN-Alkenoxypyridinium salts have been used as synthons for the umpolung reaction of enolates for the preparation of α-functionalized carbonyl compounds. In contrast, we found that the photoreduction of N-alkenoxypyridinium salts generates α-carbonyl radicals after cleavage of the N−O bond, thereby allowing simultaneous incorporation of α-keto and pyridyl groups across unactivated alkenes. In the process, the formed α-carbonyl radicals engage unactivated alkenes to afford alkyl radical intermediates poised for subsequent addition to pyridinium salts, which ultimately affords a variety of γ-pyridyl ketones under mild reaction conditions. This transformation is characterized by a broad substrate scope and good functional-group compatibility, and the utility of this transformation was further demonstrated by the late-stage functionalization of complex biorelevant molecules
URI
https://pr.ibs.re.kr/handle/8788114/7036
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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