Abstract
S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2527-2534 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 72 |
| Issue number | 20 |
| DOIs | |
| State | Published - May 19 2016 |
Keywords
- Electrochemistry
- Regioselectivity
- Unsymmetrical substitution
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Yamamoto, T., Ammam, M., Roberts, S. A., Wilson, G. S., & Glass, R. S. (2016). Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction. Tetrahedron, 72(20), 2527-2534. https://doi.org/10.1016/j.tet.2016.03.040