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Photocatalytic Multisite Functionalization of Unactivated Terminal Alkenes by Merging Polar Cycloaddition and Radical Ring‐Opening Process.

Authors :
Liu, Haidong
Wang, Yi‐Peng
Wang, Hui
Ren, Kewei
Liu, Longfei
Dang, Luzhen
Wang, Cheng‐Qiang
Feng, Chao
Source :
Angewandte Chemie International Edition. 10/7/2024, Vol. 63 Issue 41, p1-7. 7p.
Publication Year :
2024

Abstract

Although highly appealing for rapid access of molecular complexity, multi‐functionalization of alkenes that allows incorporation of more than two functional groups remains a prominent challenge. Herein, we report a novel strategy that merges dipolar cycloaddition with photoredox promoted radical ring‐opening remote C(sp3)−H functionalization, thus enabling a smooth 1,2,5‐trifunctionalization of unactivated alkenes. A highly regioselective [3+2] cycloaddition anchors a reaction trigger onto alkene substrates. The subsequent halogen atom transfer (XAT) selectively initiates ring‐opening process, which is followed by a series of 1,5‐hydrogen atom transfer (1,5‐HAT) and intermolecular fluorine atom transfer (FAT) events. With this method, site‐selective introduction of three different functional groups is accomplished and a broad spectrum of valuable β‐hydroxyl‐ϵ‐fluoro‐nitrile products are synthesized from readily available terminal alkenes. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14337851
Volume :
63
Issue :
41
Database :
Academic Search Index
Journal :
Angewandte Chemie International Edition
Publication Type :
Academic Journal
Accession number :
180045547
Full Text :
https://doi.org/10.1002/anie.202407928