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.

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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.
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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. doi:10.1039/b608410a
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.
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