meta‐C−H Bromination on Purine Bases by Heterogeneous Ruthenium Catalysis

Methods for positionally selective remote C−H functionalizations are in high demand. Herein, we disclose the first heterogeneous ruthenium catalyst for meta‐selective C−H functionalizations, which enabled remote halogenations with excellent site selectivity and ample scope. The versatile heterogeneo...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (6), p.1557-1560
Main Authors: Warratz, Svenja, Burns, David J., Zhu, Cuiju, Korvorapun, Korkit, Rogge, Torben, Scholz, Julius, Jooss, Christian, Gelman, Dmitri, Ackermann, Lutz
Format: Article
Language:English
Subjects:
Activation
Bromination
Catalysis
Catalysts
Cobalt
C−H activation
Demand
Derivatives
Fluorescence
heterogeneous catalysis
Iridium
Labels
Marking
meta selectivity
nucleobases
Palladium
Purines
Rhodium
Ruthenium
Selectivity
Silicon dioxide
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Methods for positionally selective remote C−H functionalizations are in high demand. Herein, we disclose the first heterogeneous ruthenium catalyst for meta‐selective C−H functionalizations, which enabled remote halogenations with excellent site selectivity and ample scope. The versatile heterogeneous Ru@SiO2 catalyst was broadly applicable and could be easily recovered and reused, which set the stage for the direct fluorescent labeling of purines. In contrast to palladium, rhodium, iridium, or cobalt complexes, solely the ruthenium catalysis manifold provided access to meta‐halogenated purine derivatives, illustrating the unique power of ruthenium C−H activation catalysis. Remote control: A reusable heterogeneous ruthenium complex was developed for meta‐C−H functionalization reactions on purine derivatives. Chemo‐ and positionally selective C−H halogenation reactions and diversification with a fluorescent label were thus accomplished.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201609014