This work was financially supported by a Grant-in-Aid for Scientific Research from MEXT and JSPS (Japan). We thank Dr. Yasutomo Segawa for his help in the X-ray crystal-structure analysis. S.K. thanks the International Research Training Group Münster/Nagoya for support. K.U. thanks JSPS for a predoctoral fellowship.
Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4-Selective CH Arylation Enabled by Boronic Acids†
Article first published online: 31 JAN 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 10, pages 2387–2391, March 1, 2011
How to Cite
Kirchberg, S., Tani, S., Ueda, K., Yamaguchi, J., Studer, A. and Itami, K. (2011), Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4-Selective CH Arylation Enabled by Boronic Acids. Angew. Chem. Int. Ed., 50: 2387–2391. doi: 10.1002/anie.201007060
- Issue published online: 24 FEB 2011
- Article first published online: 31 JAN 2011
- Manuscript Received: 10 NOV 2010
- JSPS (Japan)
- boronic acids;
- CH arylation;
It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new CH functionalization reaction (see scheme; TEMPO: 2,2,6,6-tetramethylpiperidine-N-oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment of Alzheimer's disease.