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Regioselectivity in C-H activation: reagent control in cyclometallation of 2-(1-naphthyl)-pyridine.

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Author

Summary, in English

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.

Publishing year

2016

Language

English

Pages

525-531

Publication/Series

Dalton Transactions

Volume

45

Issue

2

Document type

Journal article

Publisher

Royal Society of Chemistry

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1477-9234