Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions

Braun T, Izundu J, Steffen A, Neumann B, Stammler H-G (2006)
DALTON TRANSACTIONS (43): 5118-5123.

Journal Article | Published | English

No fulltext has been uploaded

Author
; ; ; ;
Abstract
The chloro and azido complexes trans-[PdCl(4-C5NF4)(PiPr(3))(2)] ( 3) and trans-[Pd(N-3)(4-C5NF4)(PiPr(3))(2)] ( 4) can be prepared by reaction of [PdF(4-C5NF4)(PiPr(3))(2)] ( 2) with Et3SiCl or MeSiN3, respectively. In contrast, reactions of 2 with Ph3SiH or Me2FSiSiFMe2 give the products of reductive elimination 2,3,5,6-tetrafluoropyridine ( 5) or 4-(fluorodimethylsilyl) tetrafluoropyridine ( 6) as well as [Pd(PiPr(3))(2)] ( 1). In a catalytic experiment, pentafluoropyridine can be converted with Ph3SiH into 5 in 62% yield, when 10% of 2 is employed as catalyst. Treatment of trans-[PdF(4-C5NF4)(PiPr(3))(2)] ( 2) with Bu3SnCH=CH2 in THF at 50 degrees C results in the formation of [Pd(PiPr(3))(2)] ( 1) and 4- vinyltetrafluoropyridine ( 7). Complex 2 is also active as a catalyst towards a Stille cross-coupling reaction of pentafluoropyridine with Bu3SnCH= CH2 to give 4-vinyltetrafluoropyridine ( 7) with a TON of 6. The molecular structure of the complex 3 has been determined by X-ray crystallography.
Publishing Year
ISSN
eISSN
PUB-ID

Cite this

Braun T, Izundu J, Steffen A, Neumann B, Stammler H-G. Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions. DALTON TRANSACTIONS. 2006;(43):5118-5123.
Braun, T., Izundu, J., Steffen, A., Neumann, B., & Stammler, H. - G. (2006). Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions. DALTON TRANSACTIONS(43), 5118-5123.
Braun, T., Izundu, J., Steffen, A., Neumann, B., and Stammler, H. - G. (2006). Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions. DALTON TRANSACTIONS, 5118-5123.
Braun, T., et al., 2006. Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions. DALTON TRANSACTIONS, (43), p 5118-5123.
T. Braun, et al., “Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions”, DALTON TRANSACTIONS, 2006, pp. 5118-5123.
Braun, T., Izundu, J., Steffen, A., Neumann, B., Stammler, H.-G.: Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions. DALTON TRANSACTIONS. 5118-5123 (2006).
Braun, Thomas, Izundu, Joseph, Steffen, Andreas, Neumann, Beate, and Stammler, Hans-Georg. “Reactivity of a palladium fluoro complex towards silanes and Bu3SnCH = CH2: catalytic derivatisation of pentafluoropyridine based on carbon-fluorine bond activation reactions”. DALTON TRANSACTIONS 43 (2006): 5118-5123.
This data publication is cited in the following publications:
This publication cites the following data publications:

4 Citations in Europe PMC

Data provided by Europe PubMed Central.

Cross coupling reactions of polyfluoroarenes via C-F activation.
Sun AD, Love JA., Dalton Trans 39(43), 2010
PMID: 20938555
Hydrometalation of fluoroallenes.
Kuhnel MF, Lentz D., Dalton Trans (24), 2009
PMID: 19513485

112 References

Data provided by Europe PubMed Central.


Huang, J. Am. Chem. Soc. 119(), 1997

Veltheer, J. Am. Chem. Soc. 117(), 1995

Huang, Angew. Chem. 109(), 1997

Huang, Angew. Chem., Int. Ed. Engl. 36(), 1997

Cooper, Inorg. Chim. Acta 270(), 1998

Tyrra, J. Organomet. Chem. 691(), 2006

Laev, Tetrahedron Lett. 38(), 1997

Laev, J. Fluorine Chem. 96(), 1999

Miller, Tetrahedron Lett. 41(), 2000

Adonin, Mendeleev Commun. (), 2000

Nilsson, Organometallics 22(), 2003

Export

0 Marked Publications

Open Data PUB

Web of Science

View record in Web of Science®

Sources

PMID: 17077884
PubMed | Europe PMC

Search this title in

Google Scholar