Palladium-catalyzed coupling reactions of bromothiophenes at the C-H bond adjacent to the sulfur atom with a new activator system, AgNO3/KF

Kei Kobayashi; Atsushi Sugie; Masabumi Takahashi; Kentaro Masui; Atsunori Mori

doi:10.1021/ol052063y

Palladium-catalyzed coupling reactions of bromothiophenes at the C-H bond adjacent to the sulfur atom with a new activator system, AgNO3/KF

Org Lett. 2005 Oct 27;7(22):5083-5. doi: 10.1021/ol052063y.

Authors

Kei Kobayashi¹, Atsushi Sugie, Masabumi Takahashi, Kentaro Masui, Atsunori Mori

Affiliation

¹ Chemical Resources Laboratory, Tokyo Institute of Technology, Yokohama, Japan.

PMID: 16235963
DOI: 10.1021/ol052063y

Abstract

[reaction: see text] Bromothiophene derivatives react with aryl iodides catalyzed by a palladium complex in the presence of a silver(I) nitrate/potassium fluoride system to induce coupling at the C-H bond, while the carbon-bromine bond is intact. The produced coupling product bearing the C-Br bond allows further palladium-catalyzed C-C bond-forming reactions in reasonable yields.