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Energy-transfer-induced [3+2] cycloadditions of N–N pyridinium ylides

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Title
Energy-transfer-induced [3+2] cycloadditions of N–N pyridinium ylides
Author(s)
Wooseok Lee; Yejin Koo; Hoimin Jung; Sukbok Chang; Sungwoo Hong
Publication Date
2023-08
Journal
Nature Chemistry, v.15, no.8, pp.1091 - 1099
Publisher
Nature Publishing Group
Abstract
Photocycloaddition is a powerful reaction to enable the conversion of alkenes into high-value synthetic materials that are normally difficult to obtain under thermal conditions. Lactams and pyridines, both prominent in pharmaceutical applications, currently lack effective synthetic strategies to combine them within a single molecular structure. Here we describe an efficient approach to diastereoselective pyridyl lactamization via a photoinduced [3+2] cycloaddition, based on the unique triplet-state reactivity of N–N pyridinium ylides in the presence of a photosensitizer. The corresponding triplet diradical intermediates allow the stepwise radical [3+2] cycloaddition with a broad range of activated and unactivated alkenes under mild conditions. This method exhibits excellent efficiency, diastereoselectivity and functional group tolerance, providing a useful synthon for ortho-pyridyl γ- and δ-lactam scaffolds with syn-configuration in a single step. Combined experimental and computational studies reveal that the energy transfer process leads to a triplet-state diradical of N–N pyridinium ylides, which promotes the stepwise cycloaddition. [Figure not available: see fulltext.]. © 2023, The Author(s), under exclusive licence to Springer Nature Limited.
URI
https://pr.ibs.re.kr/handle/8788114/13693
DOI
10.1038/s41557-023-01258-2
ISSN
1755-4330
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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