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Unlocking the Potential of & beta;-Fragmentation of Aminophosphoranyl Radicals for Sulfonyl Radical Reactions

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Title
Unlocking the Potential of & beta;-Fragmentation of Aminophosphoranyl Radicals for Sulfonyl Radical Reactions
Author(s)
Jieun Kim; Myojeong Kim; Jinwook Jeong; Sungwoo Hong
Publication Date
2023-06
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.145, no.26, pp.14510 - 14518
Publisher
AMER CHEMICAL SOC
Abstract
Exploiting & beta;-scission in aminophosphoranyl radicalsfor radical-mediatedtransformations has been a longstanding challenge. In this study,we investigated the untapped potential of & beta;-fragmentation inaminophosphoranyl radicals by leveraging the unique properties ofthe P-N bond and the substituents of P(III) reagents. Our approachcarefully considers factors such as cone angle and electronic propertiesof phosphine and employs density functional theory (DFT) calculationsto probe structural and molecular orbital influence. We successfullyinduced & beta;-fragmentation through N-S bond cleavage ofaminophosphoranyl radicals under visible light and mild conditions,generating a range of sulfonyl radicals derived from pyridinium saltsvia the photochemical activity of electron donor-acceptor (EDA)complexes. This innovative synthetic strategy exhibits broad applicability,including late-stage functionalization, and paves the way for valuablesulfonyl radical-mediated reactions, such as alkene hydrosulfonylation,difunctionalization, and pyridylic C-H sulfonylation.
URI
https://pr.ibs.re.kr/handle/8788114/13681
DOI
10.1021/jacs.3c04112
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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