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Organophotocatalytic Generation of N‐ and O‐Centred Radicals Enables Aerobic Oxyamination and Dioxygenation of Alkenes
Author(s) -
Hu XiaoQiang,
Chen Jun,
Chen JiaRong,
Yan DongMei,
Xiao WenJing
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602597
Subject(s) - chemistry , radical , pyridazine , combinatorial chemistry , catalysis , photoredox catalysis , pyrazoline , photochemistry , stereochemistry , organic chemistry , photocatalysis
A cooperative TEMPO and photoredox catalytic strategy was applied for the first time to the direct conversion of N−H and O−H bonds into N‐ and O‐centred radicals, enabling a general and selective oxidative radical oxyamination and dioxygenation of various β,γ‐unsaturated hydrazones and oximes. In the reaction, O 2 was employed not only as a terminal oxidant but also as the oxygen source. This protocol provided efficient access to the synthesis of various synthetically and biologically important pyrazoline, pyridazine and isoxazoline derivatives under metal‐free and mild reaction conditions. Mechanistic studies revealed that the cooperative organophotocatalytic system functions through two single‐electron‐transfer (SET) processes.