Journal
DALTON TRANSACTIONS
Volume 45, Issue 2, Pages 525-531Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5dt04068j
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Funding
- Swedish Research Council
- Knut and Alice Wallenberg Foundation
- Royal Physiographic Society in Lund
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2-(1-Naphthyl)-pyridine (1) possesses sp(2) C-H bonds in both the gamma- and delta-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 gamma-substitution. Electrophilic cycloborylation, on the other hand, shows unusual delta-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 gamma- and delta-substitution for palladium and gold, respectively.
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