Regioselectivity in C-H activation: reagent control in cyclometallation of 2-(1-naphthyl)-pyridine.
(2016) In Dalton Transactions 45(2). p.525-531- Abstract
- 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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/8234821
- author
- Kondrashov, Mikhail LU ; Provost, David and Wendt, Ola LU
- organization
- publishing date
- 2016
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Dalton Transactions
- volume
- 45
- issue
- 2
- pages
- 525 - 531
- publisher
- Royal Society of Chemistry
- external identifiers
-
- pmid:26597047
- wos:000367312900018
- scopus:84952793987
- pmid:26597047
- ISSN
- 1477-9234
- DOI
- 10.1039/c5dt04068j
- language
- English
- LU publication?
- yes
- id
- 48a5bb68-38f6-4704-a7b0-c583bed8404f (old id 8234821)
- date added to LUP
- 2016-04-01 10:35:29
- date last changed
- 2022-04-12 07:46:23
@article{48a5bb68-38f6-4704-a7b0-c583bed8404f, abstract = {{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.}}, author = {{Kondrashov, Mikhail and Provost, David and Wendt, Ola}}, issn = {{1477-9234}}, language = {{eng}}, number = {{2}}, pages = {{525--531}}, publisher = {{Royal Society of Chemistry}}, series = {{Dalton Transactions}}, title = {{Regioselectivity in C-H activation: reagent control in cyclometallation of 2-(1-naphthyl)-pyridine.}}, url = {{http://dx.doi.org/10.1039/c5dt04068j}}, doi = {{10.1039/c5dt04068j}}, volume = {{45}}, year = {{2016}}, }