Synlett 2022; 33(04): 346-350
DOI: 10.1055/a-1495-6994
cluster
Late-Stage Functionalization

Triazole-Enabled Ruthenium(II) Carboxylate-Catalyzed C–H Arylation with Electron-Deficient Aryl Halides

Torben Rogge
a   Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Thomas Müller
a   Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Hendrik Simon
a   Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Xiaoyan Hou
a   Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Simon Wagschal
b   Discovery Product Development and Supply, Janssen Pharmaceutica, Hochstrasse 201, 8200 Schaffhausen, Switzerland
,
Diego Broggini
b   Discovery Product Development and Supply, Janssen Pharmaceutica, Hochstrasse 201, 8200 Schaffhausen, Switzerland
,
a   Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
c   Wöhler Research Institute for Sustainable Chemistry, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
› Author Affiliations
Generous support by the DFG (SPP1807 and Gottfried-Wilhelm-Leibniz award to L.A.) and by Janssen Pharmaceutica is gratefully acknowledged.


Abstract

A triazole-directed direct C–H arylation of arenes with electron-deficient aryl halides or a synthetically useful pyrimidyl chloride was achieved through ruthenium catalysis. Our novel strategy provides operationally simple and environmentally benign access to highly functionalized hetarenes, avoiding the use of strong organometallic bases. Detailed studies revealed a significant effect of the phosphine ligand, thereby permitting the reaction to occur with excellent levels of chemo- and position selectivity.

Supporting Information



Publication History

Received: 14 April 2021

Accepted: 30 April 2021

Accepted Manuscript online:
30 April 2021

Article published online:
10 June 2021

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