Abstract
Direct C-H phenylation of 2-ethylthiophene and 2-chlorothiophene with PhPdI(bipy) complex to form either the corresponding 4-phenyl or 5-phenylthiophene derivative is studied under stoichiometric conditions using various Lewis acids as additives. It is shown that reactions occur via the corresponding cationic Pd complex (PhPdbipy +) and that the counteranion determines the regioselectivity. High-level DFT calculations reveal that C-C bond formation occurs via a carbopalladation pathway and not via electrophilic palladation. These calculations give some indications regarding the regioselectivity of the thiophene arylation.
| Original language | English |
|---|---|
| Pages (from-to) | 1256-1260 |
| Number of pages | 5 |
| Journal | Chemistry - An Asian Journal |
| Volume | 7 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2012 Jun 1 |
Keywords
- C-H activation
- DFT calculations
- catalysis
- cross-coupling
- palladium
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
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Steinmetz, M., Ueda, K., Grimme, S., Yamaguchi, J., Kirchberg, S., Itami, K., & Studer, A. (2012). Mechanistic studies on the Pd-catalyzed direct C-H arylation of 2-substituted thiophene derivatives with arylpalladium bipyridyl complexes. Chemistry - An Asian Journal, 7(6), 1256-1260. https://doi.org/10.1002/asia.201101011