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

Svenja Warratz; David J. Burns; Cuiju Zhu; Korkit Korvorapun; Torben Rogge; Julius Scholz; Christian Jooss; Dmitri Gelman; Lutz Ackermann

doi:10.1002/anie.201609014

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

Svenja Warratz, David J. Burns, Cuiju Zhu, Korkit Korvorapun, Torben Rogge, Julius Scholz, Christian Jooss, Dmitri Gelman, Lutz Ackermann^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

114 Scopus citations

Abstract

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@SiO₂catalyst 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.

Original language	American English
Pages (from-to)	1557-1560
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	6
DOIs	https://doi.org/10.1002/anie.201609014
State	Published - Feb 2017

Bibliographical note

Funding Information:
Generous support by the European Research Council under the European Community's Seventh Framework Program (FP7 2007–2013/ERC Grant agreement No. 307535), the Chinese Scholarship Program (fellowship to C.Z.), the DFG (SFB 1073 C01), and the DAAD (fellowship to K.K.) is gratefully acknowledged. Furthermore, we thank Dr. Klaus Simon (University of Göttingen) for ICP-MS analyses.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

C−H activation
heterogeneous catalysis
meta selectivity
nucleobases
ruthenium

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title = "meta-C−H Bromination on Purine Bases by Heterogeneous Ruthenium Catalysis",

abstract = "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@SiO2catalyst 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.",

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note = "Funding Information: Generous support by the European Research Council under the European Community's Seventh Framework Program (FP7 2007–2013/ERC Grant agreement No. 307535), the Chinese Scholarship Program (fellowship to C.Z.), the DFG (SFB 1073 C01), and the DAAD (fellowship to K.K.) is gratefully acknowledged. Furthermore, we thank Dr. Klaus Simon (University of G{\"o}ttingen) for ICP-MS analyses. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = feb,

doi = "10.1002/anie.201609014",

language = "American English",

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T1 - meta-C−H Bromination on Purine Bases by Heterogeneous Ruthenium Catalysis

AU - Warratz, Svenja

AU - Burns, David J.

AU - Zhu, Cuiju

AU - Korvorapun, Korkit

AU - Rogge, Torben

AU - Scholz, Julius

AU - Jooss, Christian

AU - Gelman, Dmitri

AU - Ackermann, Lutz

N1 - Funding Information: Generous support by the European Research Council under the European Community's Seventh Framework Program (FP7 2007–2013/ERC Grant agreement No. 307535), the Chinese Scholarship Program (fellowship to C.Z.), the DFG (SFB 1073 C01), and the DAAD (fellowship to K.K.) is gratefully acknowledged. Furthermore, we thank Dr. Klaus Simon (University of Göttingen) for ICP-MS analyses. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/2

Y1 - 2017/2

N2 - 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@SiO2catalyst 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.

AB - 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@SiO2catalyst 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.

KW - C−H activation

KW - heterogeneous catalysis

KW - meta selectivity

KW - nucleobases

KW - ruthenium

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JF - Angewandte Chemie - International Edition

IS - 6

ER -

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

Abstract

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Keywords

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