Regioselectivity in C-H activation: reagent control in cyclometallation of 2-(1-naphthyl)-pyridine
| Autor: | Mikhail Kondrashov, David Provost, Ola F. Wendt |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
010405 organic chemistry
Dimer Substrate (chemistry) chemistry.chemical_element Regioselectivity 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Reagent Pyridine Electrophile Organic chemistry Selectivity Palladium |
| Zdroj: | Dalton transactions (Cambridge, England : 2003). 45(2) |
| ISSN: | 1477-9234 |
| Popis: | 2-(1-Naphthyl)-pyridine () possesses sp(2) C-H bonds in both the γ- and δ-positions and is therefore a suitable substrate for studying the cyclometallation selectivity with different reagents and conditions. Such selectivity studies are reported. Based on deuterium-exchange experiments it is concluded that cycloruthenation with RuCl2(p-cymene) dimer is reversible with kinetic and thermodynamic preference for γ-substitution. Electrophilic cycloborylation, on the other hand, shows unusual δ-substitution. The previously published cyclopalladation and cycloauration of the substrate was studied in detail and was shown to be irreversible; they proceed under kinetic control and give γ- and δ-substitution for palladium and gold, respectively. |
| Databáze: | OpenAIRE |
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