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Photocatalytic Generation of N‐Centered Hydrazonyl Radicals: A Strategy for Hydroamination of β,γ‐Unsaturated Hydrazones
Author(s) -
Hu XiaoQiang,
Chen JiaRong,
Wei Qiang,
Liu FengLei,
Deng QiaoHui,
Beauchemin André M.,
Xiao WenJing
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406491
Subject(s) - hydroamination , photocatalysis , oxidizing agent , radical , chemistry , reagent , deprotonation , photochemistry , intramolecular force , amine gas treating , catalysis , organic chemistry , combinatorial chemistry , ion
A visible‐light photocatalytic generation of N‐centered hydrazonyl radicals has been accomplished for the first time. This approach allows efficient intramolecular addition of hydrazonyl radical to terminal alkenes, thus providing hydroamination and oxyamination products in good yields. Importantly, the protocol involves deprotonation of an NH bond and photocatalytic oxidation to an N‐centered radical, thus obviating the need to prepare photolabile amine precursors or the stoichiometric use of oxidizing reagents.