Volume 57, Issue 51 pp. 16903-16906
Communication

Chemoselective Pd-Catalyzed C-TeCF3 Coupling of Aryl Iodides

Theresa Sperger

Theresa Sperger

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

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Sinem Guven

Sinem Guven

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

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Prof. Dr. Franziska Schoenebeck

Corresponding Author

Prof. Dr. Franziska Schoenebeck

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

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First published: 22 October 2018
Citations: 21

Graphical Abstract

Te time: The first direct catalytic method for the formation of C(sp2)−TeCF3 bonds has been developed. It relies on a Pd/Xantphos catalytic system and allows for the trifluoromethylellurolation of aryl iodides. Computational and experimental mechanistic analyses shed light on the privileged activity of Xantphos in this transformation.

Abstract

While the TeCF3 moiety features promising properties and potential in a range of applications, no direct synthetic method exists for its incorporation into aromatic scaffolds. This report features the first direct catalytic method for the formation of C(sp2)−TeCF3 bonds. The method relies on a Pd/Xantphos catalytic system and allows for the trifluoromethyltellurolation of aryl iodides. Our computational and experimental mechanistic analyses shed light on the privileged activity of Xantphos in this transformation.

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