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In conclusion, we developed a method for the rapid synthesis of
P-perfluoroalkyl phosphines using TMDPO as a phosphorus
source. This reaction generates phosphorus(III) compounds from
phosphorus(V) species via perfluoroalkylation. This method is
viable for the synthesis of a variety of P-perfluoroalkylphosphines.
In addition, the generated P-perfluoroalkylphosphines could be
complexed with a transition-metal, platinum(II). Therefore, the
generated P-perfluoroalkylphosphines can be used as ligands, and
in the near future, new reactions are expected to be developed
using the produced P-perfluoroalkylphosphine ligand-metal
complexes.
Acknowledgment
10.
This research was supported by a Grant-in-Aid for Exploratory Research
(26620149, A.O., 26860168, S.K.), from the Ministry of Education, Culture,
Sports, Science and Technology, Japan.
Notes and references
Department of Applied Chemistry, Graduate School of Engineering, Osaka
Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531,
11.
12.
Japan.
*Corresponding
author
E-mail
(A.
Ogawa.):
Electronic Supplementary Information (ESI) available: [details
experimental procedure for the synthesis of substrates and products,
1
spectral and analytical data of products, and copies of H NMR, 13C NMR,
19F NMR, and 31P NMR spectra of products and included here]. See
DOI: 10.1039/c000000x/
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2.
3.
14.
15.
When Ph2P(O)H (0.1 mmol) was added to the reaction system in
the absence of TMDPO, byproduct nC10F21H was obtained in 10%
yield, along with the desired product in 19% yield.
4.
After the reaction, COP and POP were obtained in 6% and 81%
yields (COP, P = 30 ppm; POP, P = 29 ppm). These chemical
shifts are supported from reference 12e for COP and H. G. Korth,
J. Lusztyk and K. U. Ingold, J. Org. Chem., 1990, 55, 624-631. for
POP.
5.
6.
n
16.
17.
When Et2PH (0.2 mmol) and C10F21I (0.1 mmol) were irradiated
under the same condition in the absence of TMDPO, byproduct
nC10F21H was obtained in 13% yield, along with Et2PnC10F21 in 47%
yield.
n
When Cy2P(O)H (0.2 mmol) and C10F21I (0.1 mmol) were
irradiated under the same condition in the absence of TMDPO,
n
byproduct C10F21H was obtained in 21% yield, along with
Cy2PnC10F21 in 18% yield.
7.
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4 | J. Name., 2012, 00, 1-3
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