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 |
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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 |
Externally published | Yes |
Keywords
- C-H activation
- DFT calculations
- catalysis
- cross-coupling
- palladium
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry