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Rhodium(III)‐Catalyzed CC and CO Coupling of Quinoline N ‐Oxides with Alkynes: Combination of CH Activation with O‐Atom Transfer
Author(s) -
Zhang Xueyun,
Qi Zisong,
Li Xingwei
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.201406747
Subject(s) - catalysis , rhodium , chemistry , quinoline , oxidizing agent , medicinal chemistry , atom (system on chip) , stereochemistry , photochemistry , organic chemistry , computer science , embedded system
[Cp*Rh III ]‐catalyzed CH activation of arenes assisted by an oxidizing NO or NN directing group has allowed the construction of a number of hetercycles. In contrast, a polar NO bond is well‐known to undergo O‐atom transfer (OAT) to alkynes. Despite the liability of NO bonds in both CH activation and OAT, these two important areas evolved separately. In this report, [Cp*Rh III ] catalysts integrate both areas in an efficient redox‐neutral coupling of quinoline N ‐oxides with alkynes to afford α‐(8‐quinolyl)acetophenones. In this process the NO bond acts as both a directing group for CH activation and as an O‐atom donor.